Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

Cinchona alkaloids and their derivatives can catalyze an amazing array of synthetically important reactions, providing access to chiral products of high enantiopurity. A review of such asymmetric reactions, comprising the work reported in the last two decades, is presented here. Cinchona alkaloids-derived catalysts and ligands, either in monomeric form or attached to a polymeric support, are included in this review.

• 1 Introduction

• 2 Carbon-Carbon Bond Formation

• 2.1 Alkylation

• 2.1.1 Alkylation of Carbonyl Compounds

• 2.1.2 Alkylation of Schiff Bases: Synthesis of a-Amino Acids

• 2.2 Additions to Carbonyl Compounds

• 2.2.1 Aldol Reaction

• 2.2.2 Indium-Promoted Additions

• 2.2.3 Darzens Reaction

• 2.2.4 Baylis-Hillmann Reaction

• 2.2.5 Diethyl Zinc Addition

• 2.2.6 Michael Addition

• 2.2.7 Other Additions

• 2.3 Cycloadditions

• 2.3.1 Synthesis of β-Lactones

• 2.3.2 Synthesis of β-Lactams

• 2.3.3 Diels-Alder Reaction

• 2.4 Claisen Rearrangement

• 3 Carbon-Oxygen Bond Formation

• 3.1 Epoxidation of Enones and cis-Olefins

• 3.2 Asymmetric Dihydroxylation (AD)

• 3.3 Asymmetric Aminohydroxylation (AA)

• 3.4 α-Hydroxylation of Ketones

• 4 Hydrogenations and Reductions

• 4.1 Heterogeneous Hydrogenation of Activated Ketones

• 4.2 Heterogeneous Hydrogenation of Other Substrates

• 4.3 Homogeneous Reductions

• 5 Carbon-Heteroatom (N,P,S,F) Bond Formation

• 5.1 Chiral Aziridines and 2H-Azirines

• 5.2 Chiral α-Hydroxyphosphonate Esters

• 5.3 Chiral Sulphur Compounds

• 5.4 Chiral α-Fluorinated Carbonyl Compounds

• 6 Miscellaneous Reactions

• 6.1 Desymmetrization of Cyclic Anhydrides

• 6.2 Decarboxylation

• 7 Supported Cinchona Alkaloid Catalysts

• 7.1 Insoluble Polymer-Bound Cinchona Alkaloids

• 7.1.1 Homopolymers Derived from Cinchona Alkaloids

• 7.1.2 Copolymers of Cinchona Alkaloids with Acrylonitrile and Acrylates

• 7.1.3 Polymers of Cinchona Alkaloids with Added Spacers

• 7.1.4 Cinchona Alkaloids Catalysts Supported on Merrifield Resin

• 7.2 Cinchona Alkaloids Catalysts Immobilized on Silica Gel

• 7.3 Soluble Polymer-Bound Cinchona Ligands

• 7.4 Concluding Remarks

• Acknowledgement

• References

References

• 1 Pelletier J. Caventon JB. Ann. Chim. Phys.  1820,  14:  69 
  Google Scholar
• 2 Rabe P. Ber.  1908,  41:  62 
  Google Scholar
• 3a Prelog V. Zalan E. Helv. Chim. Acta  1944,  27:  535 
  CrossrefGoogle Scholar
• 3b Prelog V. Zalan E. Helv. Chim. Acta  1950,  33:  2021 
  CrossrefGoogle Scholar
• 4a Woodward RB. Doering WE. J. Am. Chem. Soc.  1944,  66:  849 
  CrossrefGoogle Scholar
• 4b Woodward RB. Doering WE. J. Am. Chem. Soc.  1945,  67:  860 
  CrossrefGoogle Scholar
• 5 Gates M. Sugavanam B. Schreiber SL. J. Am. Chem. Soc.  1970,  92:  205 
  CrossrefGoogle Scholar
• 6 Gutzwiller J. Uskokovic M. J. Am. Chem. Soc.  1970,  92:  204 
  CrossrefGoogle Scholar
• 7 Taylor EC. Martin SF. J. Am. Chem. Soc.  1972,  94:  6218 
  CrossrefGoogle Scholar
• 8 Imanishi T. Inoue M. Wada Y. Hanaoka M. Chem. Pharm. Bull.  1982,  30:  1925 
  Google Scholar
• 9 Trier G. In Die Alkaloide   Verlag Borntraeger; Berlin: 1931.  p.399-437  
  Google Scholar
• 10 Turner RB. Woodward RB. In The Alkaloids   Vol. III:  Manske RHF. Holmes HL. Academic Press; New York: 1953.  p.24 
  Google Scholar
• 11 Verpoorte R. Schripsema J. Van der Leer T. In The Alkaloids. Chemistry and Pharmacology   Vol. 34:  Brossi A. Academic Press; New York: 1988. 
  Google Scholar
• 12 Michael JP. The Quinoline Alkaloids, In Rodd’s Chemistry of Carbon Compounds   2nd ed., 2nd Suppl., Part F and G, Vol. IV:  Sainsbury M. Elsevier; Amsterdam: 1998.  p.432-482  
  Google Scholar
• 13a Eiden F. Pharm. Unserer Zeit  1998,  27:  257 
  Google Scholar
• 13b Eiden F. Pharm. Unserer Zeit  1999,  28:  11 
  Google Scholar
• 13c Eiden F. Pharm. Unserer Zeit  1999,  28:  74 
  Google Scholar
• 14 Newman P. Optical Resolution Procedures for Chemical Compounds   Acids, Vol.2:  Optical Resolution Information Center, Manhattan College, Riverdale; New York: 1981.  p.7-22  
  Google Scholar
• 15a Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions   Wiley; New York: 1981.  p.254 
  Google Scholar
• 15b Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions   Wiley; New York: 1981.  p.257 
  Google Scholar
• 16 Sheldon RA. Chirotechnology   Marcel Dekker; New York: 1993.  Chap. 6.
  Google Scholar
• 17a Chirality in Industry   Vol. 1:  Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1992. 
  Google Scholar
• 17b Chirality in Industry   Vol. 2:  Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1997. 
  Google Scholar
• 18 Pasteur L. C. R. Acad. Sci.  1853,  37:  162 
  Google Scholar
• 19 Wynberg H. Top. Stereochem.  1986,  16:  87 
  Google Scholar
• 20 Salvadori P. Pini D. Rosini C. Bertucci C. Uccell-Barrett G. Chirality  1992,  4:  43 
  CrossrefGoogle Scholar
• 21 Rosini C. Bertucci C. Pini D. Altemura P. Salvadori P. Chromatographia  1987,  24:  671 
  Google Scholar
• 22a Mandl A. Nicoletti L. Lammerhofer M. Lindner W. J. Chromatogr., A  1999,  858:  1 
  CrossrefGoogle Scholar
• 22b Franco P. Lammerhofer M. Klaus PM. Lindner W. J. Chromatogr., A  2000,  869:  111 
  CrossrefGoogle Scholar
• 23a Lindner W. Anal. Chem.  2000,  72:  4614 
  CrossrefGoogle Scholar
• 23b Lindner W. Anal. Chem.  2000,  72:  4623 
  CrossrefGoogle Scholar
• 24 Pracejus H. Fortschr. Chem. Forsch.  1967,  8:  493 
  Google Scholar
• 25 Morrison JD. Mosher HS. Asymmetric Organic Reactions   Prentice-Hall; Englewood Clifts: 1971. 
  Google Scholar
• 26 Aune M. Gogoll A. Matsson O. J. Org. Chem.  1995,  60:  1356 
  Google Scholar
• 27 Dijkstra GDH. Kellog RM. Wynberg H. Svendsen JS. Marko I. Sharpless KB. J. Am. Chem. Soc.  1989,  111:  8069 
  CrossrefGoogle Scholar
• 28 Dijkstra GDH. Kellog RM. Wynberg H. J. Org. Chem.  1990,  55:  6121 
  CrossrefGoogle Scholar
• 29 Shioiri T. Chiral Phase Transfer Catalysis, In Handbook of Phase Transfer Catalysis   Sasson Y. Neumann R. Blackie; London: 1997.  p.462-479  
  Google Scholar
• 30 Martyres D. Synlett  1999,  1508 
  Article in Thieme ConnectGoogle Scholar
• 31 Nelson A. Angew. Chem., Int. Ed.  1999,  38:  1583 
  CrossrefPubMedGoogle Scholar
• 32 O’Donnel MJ. Asymmetric Phase Transfer Reactions, In Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000.  p.727-755  
  Google Scholar
• 33 Hubel R. Polborn K. Beck W. Eur. J. Inorg. Chem.  1999,  471 
  Google Scholar
• 34 Lohray BB. Tetrahedron: Asymmetry  1992,  3:  1317 
  CrossrefGoogle Scholar
• 35 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev.  1994,  94:  2483 
  Google Scholar
• 36 Sharpless KB. In Transition Metal for Organic Synthesis   Vol. 2:  Beller M. Bolm C. Wiley-VCH; Weinheim: 1998.  p.219-242  
  Google Scholar
• 37 Markó IE. Svendsen JS. Dihydroxylation of Carbon-Carbon Double Bond, In Comprehensive Asymmetric Catalysis   Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  p.713-784  
  Google Scholar
• 38a Johnson RA. Sharpless KB. Catalytic Asymmetric Dihydroxylation - Discovery and Development, In Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000.  Chap. 6D. p.357-398  
  Google Scholar
• 38b Bolm C. Hildebrand JP. Muniz K. Recent Advances in AD and AA, In Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000.  Chap. 6E. p.399-428  
  Google Scholar
• 39 Blaser HU. Tetrahedron: Asymmetry  1991,  2:  843 
  CrossrefGoogle Scholar
• 40 Blaser HU. Jalett HP. Müller M. Studer M. Catal. Today  1997,  37:  441 
  CrossrefGoogle Scholar
• 41 Baiker A. Blaser HU. Cinchona-Modified Platinum Hydrogenation Catalysts and Related Systems, In Handbook of Heterogeneous Catalysis   Ertl G. Knozinger H. Weitkamp J. VCH; Weinheim: 1997.  p.2425-2436  
  Google Scholar
• 42 Dolling U.-H. Davis P. Grabowski EJJ. J. Am. Chem. Soc.  1984,  106:  446 
  CrossrefGoogle Scholar
• 43a Dolling U.-H, Grabowski EJJ, and Pines SH. inventors; Eur. Pat. Appl. EP.  121,872. 
• 44 Hughes DL. Dolling U.-H. Ryan KM. Schoenewaldt EF. Grabowski EJJ. J. Org. Chem.  1987,  52:  4745 
  CrossrefGoogle Scholar
• 45 Bhattacharya A. Dolling U.-H. Grabowski EJJ. Karady S. Ryan KM. Weinstock LM. Angew. Chem., Int. Ed. Engl.  1986,  25:  476 
  CrossrefGoogle Scholar
• 46 Conn RSE. Lovell AV. Karady S. Weinstock LM. J. Org. Chem.  1986,  51:  4710 
  CrossrefGoogle Scholar
• 47a Conn RSE, and Karady S. inventors; US Patent  4,704,472. 
• 48 Nerinckx W. Vandewalle M. Tetrahedron: Asymmetry  1990,  1:  265 
  CrossrefGoogle Scholar
• 49 Arai S. Oku M. Ishida T. Shioiri T. Tetrahedron Lett.  1999,  40:  6785 
  CrossrefGoogle Scholar
• 50 Lee TBK. Wong GSK. J. Org. Chem.  1991,  56:  872 
  CrossrefGoogle Scholar
• 51 Corey EJ. Bo Y. Busch-Petersen J. J. Am. Chem. Soc.  1998,  120:  13000 
  CrossrefGoogle Scholar
• 52 O’Donnell MJ. Esikova IA. Mi A. Shullenberger DF. Wu S. Amino Acid and Peptide Synthesis Using Phase-Transfer Catalysis, In Phase-Transfer Catalysis: Mechanisms and Synthesis   Halpern ME. ACS Symposium Series 659; Washington: 1997.  Chap. 10.
  Google Scholar
• 53 O’Donnell MJ. Bennett WD. Wu S. J. Am. Chem. Soc.  1989,  111:  2353 
  CrossrefGoogle Scholar
• 54 Lipkowitz KB. Cavanaugh MW. Baker B. O’Donnell MJ. J. Org. Chem.  1991,  56:  5181 
  CrossrefGoogle Scholar
• 55 O’Donnell MJ. Wu S. Huffman JC. Tetrahedron  1994,  50:  4507 
  CrossrefGoogle Scholar
• 56 O’Donnell MJ. Delgado F. Pottrof RS. Tetrahedron  1999,  55:  6347 
  CrossrefGoogle Scholar
• 57 Lygo B. Wainwright PG. Tetrahedron Lett.  1997,  38:  8595 
  CrossrefGoogle Scholar
• 58 Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc.  1997,  119:  12414 
  CrossrefGoogle Scholar
• 59 O’Donnell MJ. Delgado F. Hostettler C. Schwesinger R. Tetrahedron Lett.  1998,  39:  8775 
  CrossrefGoogle Scholar
• 60 Imperiali B. Prins JT. Fisher SL. J. Org. Chem.  1993,  58:  1613 
  Google Scholar
• 61 Imperiali B. Fisher SL. J. Org. Chem.  1992,  57:  757 
  Google Scholar
• 62 Imperiali B. Roy RS. J. Org. Chem.  1995,  60:  1891 
  Google Scholar
• 63 Lygo B. Tetrahedron Lett.  1999,  40:  1389 
  CrossrefGoogle Scholar
• 64 Lygo B. Crosby J. Peterson JA. Tetrahedron Lett.  1999,  40:  1385 
  CrossrefGoogle Scholar
• 65 Torrado A. Imperiali B. J. Org. Chem.  1996,  61:  8940 
  CrossrefGoogle Scholar
• 66 O’Donnell MJ. Wu S. Tetrahedron: Asymmetry  1992,  3:  591 
  CrossrefGoogle Scholar
• 67 Lygo B. Crosby J. Peterson JA. Tetrahedron Lett.  1999,  40:  8671 
  CrossrefGoogle Scholar
• 68 Gasparski CM. Miller MJ. Tetrahedron  1991,  47:  5367 
  CrossrefGoogle Scholar
• 69 Horikawa M. Petersen-Busch J. Corey EJ. Tetrahedron Lett.  1999,  40:  3843 
  CrossrefGoogle Scholar
• 70 Ando A. Miura T. Tatematsu T. Shioiri T. Tetrahedron Lett.  1993,  34:  1507 
  CrossrefGoogle Scholar
• 71 Shioiri T. Bohsako A. Ando A. Heterocycles  1996,  42:  93 
  Google Scholar
• 72 Corey EJ. Zhang F.-Y. Angew. Chem., Int. Ed.  1999,  38:  1931 
  CrossrefGoogle Scholar
• 73 Johar PS. Araki S. Butsugan Y. J. Chem. Soc., Perkin Trans. 1  1992,  711 
  CrossrefGoogle Scholar
• 74 Loh T.-P. Zhou J.-R. Li X.-R. Tetrahedron Lett.  1999,  40:  9333 
  CrossrefGoogle Scholar
• 75 Loh T.-P. Zhou J.-R. Yin Z. Org. Lett.  1999,  1:  1855 
  Google Scholar
• 76 Hummelen JC. Wynberg H. Tetrahedron Lett.  1978,  1089 
  CrossrefGoogle Scholar
• 77 Arai S. Shioiri T. Tetrahedron Lett.  1998,  39:  2145 
  CrossrefGoogle Scholar
• 78 Arai S. Ishida T. Shioiri T. Tetrahedron Lett.  1998,  39:  8299 
  CrossrefGoogle Scholar
• 79 Arai S. Shirai Y. Ishida T. Shioiri T. Chem. Commun.  1999,  49 
  CrossrefGoogle Scholar
• 80 Arai S. Shirai Y. Ishida T. Shioiri T. Tetrahedron  1999,  55:  6375 
  CrossrefGoogle Scholar
• 81 Drewes SE. Roos GHP. Tetrahedron  1988,  44:  4653 
  CrossrefGoogle Scholar
• 82 Gilbert A. Heritage TW. Isaacs NS. Tetrahedron: Asymmetry  1991,  2:  969 
  CrossrefGoogle Scholar
• 83 Basaviah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
  CrossrefGoogle Scholar
• 84 Roth F. Gygax P. Fráter G. Tetrahedron Lett.  1992,  33:  1045 
  CrossrefGoogle Scholar
• 85 Iwabuchi Y. Nakatani M. Yokoyama N. Hatakeyama S. J. Am. Chem. Soc.  1999,  121:  10219 
  CrossrefGoogle Scholar
• 86 Soai K. Niwa S. Chem. Rev.  1992,  92:  833 
  CrossrefGoogle Scholar
• 87 Smaardijk AA. Wynberg H. J. Org. Chem.  1987,  52:  135 
  CrossrefGoogle Scholar
• 88 Muchow G. Vannoorenberghe Y. Bouno G. Tetrahedron Lett.  1987,  28:  6163 
  CrossrefGoogle Scholar
• 89 Oeveren A. Menge W. Feringa B. Tetrahedron Lett.  1989,  30:  6427 
  CrossrefGoogle Scholar
• 90 Brunner H. Bügler J. Bull. Soc. Chim. Belg.  1997,  106:  77 
  Google Scholar
• 91 Blaser HU. Jalett HP. Lottenbach W. Studer M. J. Am. Chem. Soc.  2000,  122:  12675 
  CrossrefGoogle Scholar
• 92 Oare DA. Heathcock CH. Top. Stereochem.  1989,  19:  242 
  Google Scholar
• 93 Kaneko S. Yoshino T. Katoh T. Terashima S. Heterocycles  1997,  46:  27 
  Google Scholar
• 94 Kaneko S. Yoshino T. Katoh T. Terashima S. Tetrahedron  1998,  54:  5471 
  CrossrefGoogle Scholar
• 95 Arai S. Nakayama K. Ishida T. Shioiri T. Tetrahedron Lett.  1999,  40:  4215 
  CrossrefGoogle Scholar
• 96 Loupy A. Sansoulet J. Zaparucha A. Merienne C. Tetrahedron Lett.  1989,  30:  333 
  CrossrefGoogle Scholar
• 97 Heisler T. Janowski WK. Prager RH. Thompson MJ. Aust. J. Chem.  1989,  42:  37 
  Google Scholar
• 98 Brunner H. Krumey C. J. Mol. Catal. A.: Chem.  1999,  142:  7 
  CrossrefGoogle Scholar
• 99 Corey EJ. Noe MC. Xu F. Tetrahedron Lett.  1998,  39:  5347 
  CrossrefGoogle Scholar
• 100 Zhang F.-Y. Corey EJ. Org. Lett.  2000,  2:  1097 
  CrossrefPubMedGoogle Scholar
• 101 Perrard T. Plaquevent J.-C. Desmurs J.-R. Hebrault D. Org. Lett.  2000,  2:  2959 
  CrossrefGoogle Scholar
• 102 Iseki K. Nagai T. Kobayashi Y. Tetrahedron Lett.  1994,  35:  3137 
  CrossrefGoogle Scholar
• 103 Iseki K. Tetrahedron  1998,  54:  13887 
  CrossrefGoogle Scholar
• 104 Huffman MA. Yasuda N. DeCamp AE. Grabowski EJJ. J. Org. Chem.  1995,  60:  1590 
  CrossrefGoogle Scholar
• 105 Arai S. Hamaguchi S. Shioiri T. Tetrahedron Lett.  1998,  39:  2997 
  CrossrefGoogle Scholar
• 106 Wynberg H. Staring EGJ. J. Am. Chem. Soc.  1982,  104:  166 
  CrossrefGoogle Scholar
• 107 Tennyson R. Romo D. J. Org. Chem.  2000,  65:  7248 
  CrossrefGoogle Scholar
• 108 Wynberg H. Staring EGJ. J. Org. Chem.  1985,  50:  1977 
  CrossrefGoogle Scholar
• 109 Ketelaar PEF. Staring EGJ. Wynberg H. Tetrahedron Lett.  1985,  26:  4665 
  CrossrefGoogle Scholar
• 110 Stutte P. The Preparation and Uses of Enantiomerically Pure β-Lactones, In Chirality in Industry   Vol. 1:  Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1992.  p.341-348  
  Google Scholar
• 111 Song CE. Lee JK. Lee SH. Lee S. Tetrahedron: Asymmetry  1995,  6:  1063 
  CrossrefGoogle Scholar
• 112 Song CE. Lee JK. O’Kim I. Choi JH. Synth. Commun.  1997,  27:  1009 
  CrossrefGoogle Scholar
• 113 Staring EGJ. Moorlag H. Wynberg H. Recl. Trav. Chim. Pays-Bas  1986,  105:  374 
  Google Scholar
• 114 Fujisawa T. Ito T. Fujimoto K. Shimizu M. Wynberg H. Staring EGJ. Tetrahedron Lett.  1997,  38:  1593 
  CrossrefGoogle Scholar
• 115 Wynberg H. Staring EGJ. J. Chem. Soc., Chem. Commun.  1984,  1181 
  CrossrefGoogle Scholar
• 116 Calter MA. J. Org. Chem.  1996,  61:  8006 
  CrossrefGoogle Scholar
• 117 Calter MA. Guo X. J. Org. Chem.  1998,  63:  5308 
  CrossrefGoogle Scholar
• 118 Calter MA. Bi FC. Org. Lett.  2000,  2:  1529 
  CrossrefGoogle Scholar
• 119 Taggi AE. Hafez AM. Wack H. Young B. Drury WJ. Lectka T. J. Am. Chem. Soc.  2000,  122:  7831 
  CrossrefGoogle Scholar
• 120 Riant O. Kagan HB. Tetrahedron Lett.  1989,  30:  7403 
  Google Scholar
• 121 Riant O. Kagan HB. Ricard L. Tetrahedron  1994,  50:  4543 
  CrossrefGoogle Scholar
• 122 Okamura H. Morishige K. Iwagawa T. Nakatani M. Tetrahedron Lett.  1998,  39:  1211 
  CrossrefGoogle Scholar
• 123 Okamura H. Shimizu H. Nakamura Y. Iwagawa T. Nakatani M. Tetrahedron Lett.  2000,  41:  4147 
  CrossrefGoogle Scholar
• 124 Okamura H. Nakamura Y. Iwagawa T. Nakatani M. Chem. Lett.  1996,  193 
  CrossrefGoogle Scholar
• 125 Kazmaier U. Krebs A. Angew. Chem., Int. Ed. Engl.  1995,  34:  2012 
  CrossrefGoogle Scholar
• 126 Kazmaier U. Krebs A. Tetrahedron Lett.  1996,  37:  7945 
  CrossrefGoogle Scholar
• 127 Mues H. Kazmaier U. Synlett  2000,  1004 
  Article in Thieme ConnectGoogle Scholar
• 128 Lygo B. Wainwright PG. Tetrahedron Lett.  1998,  39:  1599 
  CrossrefGoogle Scholar
• 129 Corey EJ. Zhang F.-Y. Org. Lett.  1999,  1:  1287 
  CrossrefPubMedGoogle Scholar
• 131 Arai S. Tsuge H. Shioiri T. Tetrahedron Lett.  1998,  39:  7563 
  CrossrefGoogle Scholar
• 132 Pluim H. Wynberg H. J. Org. Chem.  1980,  45:  2498 
  CrossrefGoogle Scholar
• 133 Arai S. Oku M. Miura M. Shioiri T. Synlett  1998,  1201 
  Article in Thieme ConnectGoogle Scholar
• 134 Wynberg H. Marsman B. J. Org. Chem.  1980,  45:  158 
  Google Scholar
• 135 Alcaraz L. Macdonald G. Ragot JP. Lewis N. Taylor RJK. J. Org. Chem.  1998,  63:  3526 
  CrossrefGoogle Scholar
• 136 Macdonald G. Alcaraz L. Lewis NJ. Taylor RJK. Tetrahedron Lett.  1998,  39:  5433 
  CrossrefGoogle Scholar
• 137 Chang S. Galvin JM. Jacobsen EN. J. Am. Chem. Soc.  1994,  116:  6937 
  CrossrefGoogle Scholar
• 138 Lygo B. Wainwright PG. Tetrahedron  1999,  55:  6289 
  CrossrefGoogle Scholar
• 139 Sharpless KB. Amberg W. Beller M. Chen H. Hartung J. Kawanami Y. Lübben D. Manoury E. Ogino Y. Shibata T. Ukita T. J. Org. Chem.  1991,  56:  4585 
  CrossrefGoogle Scholar
• 140 Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D. Zhang X.-L. J. Org. Chem.  1992,  57:  2768 
  Google Scholar
• 141 Crispino GA. Jeong K.-S. Kolb HC. Wang Z.-M. Xu D. Sharpless KB. J. Org. Chem.  1993,  58:  3785 
  CrossrefGoogle Scholar
• 142 Amberg W. Bennani YL. Chadha RK. Crispino GA. Davis WD. Hartung J. Jeong K.-S. Ogino Y. Shibata T. Sharpless KB. J. Org. Chem.  1993,  58:  844 
  CrossrefGoogle Scholar
• 143 Becker H. King SB. Taniguchi M. Vanhessche KPM. Sharpless KB. J. Org. Chem.  1995,  60:  3940 
  CrossrefGoogle Scholar
• 144 Becker H. Sharpless KB. Angew. Chem., Int. Ed. Engl.  1996,  35:  448 
  CrossrefGoogle Scholar
• 145 Wang L. Sharpless KB. J. Am. Chem. Soc.  1992,  114:  7568 
  CrossrefGoogle Scholar
• 146 Corey EJ. Noe MC. J. Am. Chem. Soc.  1993,  115:  12579 
  Google Scholar
• 147 Corey EJ. Noe MC. Sarshar S. J. Am. Chem. Soc.  1993,  115:  3828 
  CrossrefGoogle Scholar
• 148 Crispino GA. Makita A. Wang Z.-M. Sharpless KB. Tetrahedron Lett.  1994,  35:  543 
  CrossrefGoogle Scholar
• 149 Lohray BB. Bhushan V. Tetrahedron Lett.  1992,  33:  5113 
  CrossrefGoogle Scholar
• 150 Wang X. Zak M. Maddess M. O’Shea P. Tillyer R. Grabowski EJJ. Reider PJ. Tetrahedron Lett.  2000,  41:  4865 
  CrossrefGoogle Scholar
• 151 Krysan DJ. Tetrahedron Lett.  1996,  37:  1375 
  CrossrefGoogle Scholar
• 152 Corey EJ. Noe MC. Lin S. Tetrahedron Lett.  1995,  36:  8741 
  CrossrefGoogle Scholar
• 153 Corey EJ. Noe MC. Ting AY. Tetrahedron Lett.  1996,  37:  1735 
  CrossrefGoogle Scholar
• 154 Dobler C. Mehltretter GM. Sundermeier U. Beller M. J. Am. Chem. Soc.  2000,  122:  10289 
  CrossrefGoogle Scholar
• 155 Arrington MP. Bennani YL. Göbel T. Walsh P. Zhao S.-H. Sharpless KB. Tetrahedron Lett.  1993,  34:  7375 
  CrossrefGoogle Scholar
• 156 Kolb HC. Andersson PG. Bennani YL. Crispino GA. Jeong K.-S. Kwong H.-L. Sharpless KB. J. Am. Chem. Soc.  1993,  115:  12226 
  CrossrefGoogle Scholar
• 157 Li G. Sharpless KB. Acta Chem. Scand.  1996,  50:  649 
  CrossrefGoogle Scholar
• 158 Song CE. Oh CR. Roh EJ. Lee S. Choi JH. Tetrahedron: Asymmetry  1999,  10:  671 
  CrossrefGoogle Scholar
• 159 Tao B. Schlingloff G. Sharpless KB. Tetrahedron Lett.  1998,  39:  2507 
  CrossrefGoogle Scholar
• 160 Bruncko M. Schlingloff G. Sharpless KB. Angew. Chem., Int. Ed. Engl.  1997,  36:  1483 
  CrossrefGoogle Scholar
• 161 O’Brien P. Angew. Chem., Int. Ed.  1999,  38:  326 
  CrossrefGoogle Scholar
• 162 Goossen LJ. Liu H. Dress R. Sharpless KB. Angew. Chem., Int. Ed.  1999,  38:  1080 
  CrossrefGoogle Scholar
• 163 O’Brien P. Osborne SA. Parker DD. J. Chem. Soc., Perkin. Trans. 1  1998,  2519 
  CrossrefGoogle Scholar
• 164 Raatz D. Innertsberger C. Reiser O. Synlett  1999,  1907 
  Article in Thieme ConnectGoogle Scholar
• 165 Sharpless KB. In Transition Metal for Organic Synthesis Vol. 2:  Beller M. Bolm C. Wiley-VCH; Weinheim: 1998.  p.243-260  
• 166 Phukan P. Sudalai A. Tetrahedron: Asymmetry  1998,  9:  1001 
  CrossrefGoogle Scholar
• 167 Reddy KL. Sharpless KB. J. Am. Chem. Soc.  1998,  120:  1207 
  CrossrefGoogle Scholar
• 168 Morgan AJ. Masse CE. Panek JS. Org. Lett.  1999,  1:  1949 
  CrossrefGoogle Scholar
• 169 Masui M. Ando A. Shioiri T. Tetrahedron Lett.  1988,  29:  2835 
  CrossrefGoogle Scholar
• 170 Orito Y. Imai S. Niwa S. Nguyen G.-H. J. Synth. Org. Chem. Jpn.  1979,  37:  173 
  Google Scholar
• 171 Orito Y. Imai S. Niwa S. J. Chem. Soc. Jpn.  1979,  1118 
  Google Scholar
• 172 Zuo X. Liu H. Liu M. Tetrahedron Lett.  1998,  39:  1941 
  CrossrefGoogle Scholar
• 173 Blaser HU. Jalett HP. Wiehl J. J. Mol. Cat.  1991,  68:  215 
  Google Scholar
• 174 Blaser HU. Jalett H.-P. Spindler F. J. Mol. Cat. A: Chem.  1996,  107:  85 
  Google Scholar
• 175 LeBlond C. Wang J. Liu J. Andrews AT. Sun Y.-K. J. Am. Chem. Soc.  1999,  121:  4920 
  CrossrefGoogle Scholar
• 176 Blaser H.-U. Garland M. J. Am. Chem. Soc.  1990,  112:  7048 
  CrossrefGoogle Scholar
• 177 Studer M. Burkhardt S. Indolese AF. Blaser HU. Chem. Commun.  2000,  1327 
  CrossrefGoogle Scholar
• 178 Herold P. Indolese AF. Studer M. Jalett HP. Siegrist U. Blaser HU. Tetrahedron  2000,  56:  6497 
  CrossrefGoogle Scholar
• 179 Török B. Balázsik K. Szöllösi G. Felföldi K. Bartók M. Chirality  1999,  11:  470 
  CrossrefGoogle Scholar
• 180 vonArx M. Mallat T. Baiker A. J. Catal.  2000,  193:  161 
  CrossrefGoogle Scholar
• 181 Wang G.-Z. Mallat T. Baiker A. Tetrahedron: Asymmetry  1997,  8:  2133 
  CrossrefGoogle Scholar
• 182 Török B. Felföldi K. Balazsik K. Bartok M. Chem. Commun.  1999,  1725 
  CrossrefGoogle Scholar
• 183 Studer M. Burkhard S. Blaser HU. Chem. Commun.  1999,  1727 
  CrossrefGoogle Scholar
• 184 Szabo A. Künzle N. Mallat T. Baiker A. Tetrahedron: Asymmetry  1999,  10:  61 
  CrossrefGoogle Scholar
• 185 Künzle N. Szabo A. Schürch M. Wang G. Mallat T. Baiker A. Chem. Commun.  1998,  1377 
  CrossrefGoogle Scholar
• 186 Schürch M. Schwalm O. Mallat T. Weber J. Baiker A. J. Catal.  1997,  169:  275 
  CrossrefGoogle Scholar
• 187 Schürch M. Künzle N. Mallat T. Baiker A. J. Catal.  1998,  176:  569 
  CrossrefGoogle Scholar
• 188 Balazsik K. Szöri K. Felföldi K. Török B. Bartok M. Chem. Commun.  2000,  555 
  CrossrefGoogle Scholar
• 189 Vermeer WAH. Fulford A. Johnston P. Wells PB. J. Chem. Soc., Chem. Commun.  1993,  1053 
  CrossrefGoogle Scholar
• 190 Zuo X. Liu H. Tian J. J. Mol. Cat. A: Chem.  2000,  157:  217 
  Google Scholar
• 191 Slipszenko JA. Griffiths SP. Jonhston P. Simons KE. Vermeer WAH. Wells PB. J. Catal.  1998,  179:  267 
  CrossrefGoogle Scholar
• 192 Studer M. Okafor V. Blaser HU. Chem. Commun.  1998,  1053 
  CrossrefGoogle Scholar
• 193 Lipkin D. Stewart TD. J. Am. Chem. Soc.  1939,  61:  3295 
  CrossrefGoogle Scholar
• 194 Borszeky K. Bürgi T. Zhaohui Z. Mallat T. Baiker A. J. Catal.  1999,  187:  160 
  CrossrefGoogle Scholar
• 195 Borszeky K. Mallat T. Baiker A. Tetrahedron: Asymmetry  1997,  8:  3745 
  CrossrefGoogle Scholar
• 196 Nitta Y. Kobiro K. Chem. Lett.  1996,  897 
  Google Scholar
• 197 Borszeky K. Mallat T. Baiker A. Catal. Lett.  1999,  59:  95 
  CrossrefGoogle Scholar
• 198 Borszeky K. Mallat T. Baiker A. Tetrahedron: Asymmetry  1999,  10:  4781 
  CrossrefGoogle Scholar
• 199 Blaser HU. Boyer SK. Pittelkow U. Tetrahedron: Asymmetry  1991,  2:  721 
  CrossrefGoogle Scholar
• 200 » ervinka O. Collect. Czech. Chem. Commun.  1965,  30:  1684 
  Google Scholar
• 201 »ervinka O. KŻiž O. Collect. Czech. Chem. Commun.  1973,  38:  294 
  Google Scholar
• 202 »ervinka O. Fábryová A. Sablukova I. Collect. Czech. Chem. Commun.  1986,  51:  401 
  Google Scholar
• 203 Colonna S. Fornasier R. J. Chem. Soc., Perkin Trans. 1  1978,  371 
  CrossrefGoogle Scholar
• 204 Pochapsky TC. Stone PM. J. Am. Chem. Soc.  1991,  113:  1460 
  CrossrefGoogle Scholar
• 205 Hofstetter C. Wilkinson P. Pochapsky TC. J. Org. Chem.  1999,  64:  8794 
  CrossrefGoogle Scholar
• 206 Baiker A. J. Mol. Cat. A: Chem.  1997,  115:  473 
  Google Scholar
• 207 Blaser H.-U. Jalett H.-P. Garland M. Studer M. Thies H. Wirth-Tijani A. J. Catal.  1998,  173:  282 
  CrossrefGoogle Scholar
• 208 Bartók M. Felföldi K. Szöllösi G. Bartók T. Catal. Lett.  1999,  61:  1 
  CrossrefGoogle Scholar
• 209 Bartók M. Felföldi K. Szöllösi G. Bartók T. React. Kinet. Catal. Lett.  1999,  68:  371 
  Google Scholar
• 210 Ferri D. Bürgi T. Borszeky K. Mallat T. Baiker A. J. Catal.  2000,  193:  139 
  CrossrefGoogle Scholar
• 211 Bönnemann H. Braun GA. Chem.-Eur. J.  1997,  3:  1200 
  Google Scholar
• 212 Zuo X. Liu H. Guo D. Yang X. Tetrahedron  1999,  55:  7787 
  CrossrefGoogle Scholar
• 213 Collier PJ. Iggo JA. Whyman R. J. Mol. Cat. A: Chem.  1999,  146:  149 
  Google Scholar
• 214 Simons KE. Ibbotson A. Johnston P. Plum H. Wells PB. J. Catal.  1994,  150:  321 
  CrossrefGoogle Scholar
• 215 Zuo X. Liu H. Yue C. J. Mol. Cat. A: Chem.  1999,  147:  63 
  Google Scholar
• 216 Wells PB. Simons KE. Slipszenko JA. Griffiths SP. Ewing DF. J. Mol. Cat. A: Chem.  1999,  146:  159 
  Google Scholar
• 217 Aires-de-Sousa J. Lobo AM. Prabhakar S. Tetrahedron Lett.  1996,  37:  3183 
  CrossrefGoogle Scholar
• 218 Verstappen MMH. Ariaans GJA. Zwanenburg B. J. Am. Chem. Soc.  1996,  118:  8491 
  CrossrefGoogle Scholar
• 219 Palacios F. Ochoa de Retana AM. Gil JI. Tetrahedron Lett.  2000,  41:  5363 
  CrossrefGoogle Scholar
• 220 Palacios F. Ochoa de Retana AM. Gil JI. Ezpeleta JM. J. Org. Chem.  2000,  65:  3213 
  CrossrefGoogle Scholar
• 221 Wynberg H. Smaardijk AA. Tetrahedron Lett.  1983,  24:  5899 
  CrossrefGoogle Scholar
• 222 Smaardijk AA. Noorda S. Bolhuis F. Wynberg H. Tetrahedron Lett.  1985,  26:  493 
  CrossrefGoogle Scholar
• 223 MikoŠajczyk M. Drabowicz J. KieŠbasiŇ ski P. Formation of C-S Bond, In Stereoselective Synthesis   Vol. 8:  Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1996.  p.5017 
  Google Scholar
• 224 Shibasaki M. Nishida A. Ikegami S. J. Chem. Soc., Chem. Commun.  1982,  1324 
  CrossrefGoogle Scholar
• 225 Gawroński JK. Gawrońska K. KoŠbon H. Wynberg H. Recl. Trav. Chim. Pays-Bas  1983,  102:  479 
  Google Scholar
• 226 Kumar A. Salunkhe RV. Ramkrishna AR. Dike SY. J. Chem. Soc., Chem. Commun.  1991,  485 
  CrossrefGoogle Scholar
• 227 Yamashita H. Mukaiyama T. Chem. Lett.  1985,  363 
  Google Scholar
• 228 Faber WS. Kok J. deLange B. Feringa BL. Tetrahedron  1994,  50:  4775 
  CrossrefGoogle Scholar
• 229 Drabowicz J. LegÍdü S. Mikoajczyk M. Tetrahedron  1988,  44:  5243 
  CrossrefGoogle Scholar
• 230 Shibata N. Suzuki E. Takeuchi Y. J. Am. Chem. Soc.  2000,  122:  10728 
  CrossrefGoogle Scholar
• 232 Hiratake J. Inagaki M. Yamamoto Y. Oda J. J. Chem. Soc., Perkin Trans. 1  1987,  1053 
  CrossrefGoogle Scholar
• 233 Bolm C. Gerlach A. Dinter CL. Synlett  1999,  195 
  Article in Thieme ConnectGoogle Scholar
• 234 Bolm C. Schiffers I. Dinter CL. Gerlach A. J. Org. Chem.  2000,  65:  6984 
  CrossrefGoogle Scholar
• 235 Chen Y. Tian S.-K. Deng L. J. Am. Chem. Soc.  2000,  122:  9542 
  CrossrefGoogle Scholar
• 236 Aitken RA. Gopal J. Tetrahedron: Asymmetry  1990,  1:  517 
  CrossrefGoogle Scholar
• 237 Bernardi A. Arosio D. Dellavecchia D. Micheli F. Tetrahedron: Asymmetry  1999,  10:  3403 
  CrossrefGoogle Scholar
• 238 Hashimoto K. Kitaguchi J. Mizuno Y. Kobayashi T. Shirahama H. Tetrahedron Lett.  1996,  37:  2275 
  CrossrefGoogle Scholar
• 239 Aitken RA. Gopal J. Hirst JA. J. Chem. Soc., Chem. Commun.  1988,  632 
  CrossrefGoogle Scholar
• 240 Toussaint O. Capdevielle P. Maumy M. Tetrahedron Lett.  1987,  28:  539 
  CrossrefGoogle Scholar
• 241 Brunner H. Kurzwart M. Monatsh. Chem.  1992,  123:  121 
  CrossrefGoogle Scholar
• 242 Brunner H. Müller J. Spitzer J. Monatsh. Chem.  1996,  127:  845 
  CrossrefGoogle Scholar
• 243 Brunner H. Schmidt P. Prommesberger M. Tetrahedron: Asymmetry  2000,  11:  1501 
  CrossrefGoogle Scholar
• 244 Brunner H. Schmidt P. Eur. J. Org. Chem.  2000,  2119 
  CrossrefGoogle Scholar
• 245 Shuttleworth SJ. Allin SM. Sharma PK. Synthesis  1997,  1217 
  Article in Thieme ConnectGoogle Scholar
• 246 Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis  2000,  1035 
  Article in Thieme ConnectGoogle Scholar
• 247 Bhalay G. Dunstan A. Glen A. Synlett  2000,  1846 
  Article in Thieme ConnectGoogle Scholar
• 248 Salvadori P. Pini D. Petri A. Synlett  1999,  1181 
  Article in Thieme ConnectGoogle Scholar
• 249 Bolm C. Gerlach A. Eur. J. Org. Chem.  1998,  21 
  CrossrefGoogle Scholar
• 250 Kobayashi N. Iwai K. J. Am. Chem. Soc.  1978,  100:  7071 
  CrossrefGoogle Scholar
• 251 Song CE. Ryu TH. Roh EJ. Kim IO. Ha H.-J. Tetrahedron: Asymmetry  1994,  5:  1215 
  CrossrefGoogle Scholar
• 252 Canali L. Song CE. Sherrington DC. Tetrahedron: Asymmetry  1998,  9:  1029 
  CrossrefGoogle Scholar
• 253 Lohray BB. Thomas A. Chittari P. Ahuja JR. Dhal PK. Tetrahedron Lett.  1992,  33:  5453 
  CrossrefGoogle Scholar
• 254 Song CE. Roh EJ. Lee S. Kim IO. Tetrahedron: Asymmetry  1995,  6:  2687 
  CrossrefGoogle Scholar
• 255 Yamashita T. Yasueda H. Miyauchi Y. Nakamura N. Bull. Chem. Soc. Jpn.  1977,  50:  1532 
  Google Scholar
• 256 Kobayashi N. Iwai K. J. Polym. Sci., Polym. Chem. Ed.  1980,  18:  223 
  CrossrefGoogle Scholar
• 257 Kobayashi N. Iwai K. Tetrahedron Lett.  1980,  21:  2167 
  CrossrefGoogle Scholar
• 258 Danda H. Chino K. Wake S. Chem. Lett.  1991,  731 
  Google Scholar
• 259 Inagaki M. Hatanaka A. Mimura M. Hiratake J. Nishioka T. Oda J. Bull. Chem. Soc. Jpn.  1992,  65:  111 
  Google Scholar
• 260 Lohray BB. Nandanan E. Bhushan V. Tetrahedron Lett.  1994,  35:  6559 
  CrossrefGoogle Scholar
• 261 Nandanan E. Sudalai A. Ravindranathan T. Tetrahedron Lett.  1997,  38:  2577 
  CrossrefGoogle Scholar
• 262 Pini D. Petri A. Nardi A. Rosini C. Salvadori P. Tetrahedron Lett.  1991,  32:  5175 
  CrossrefGoogle Scholar
• 263 Inagaki M. Hiratake J. Yamamoto Y. Oda J. Bull. Chem. Soc. Jpn.  1987,  60:  4121 
  CrossrefGoogle Scholar
• 264 Kim BM. Sharpless KB. Tetrahedron Lett.  1990,  31:  3003 
  CrossrefGoogle Scholar
• 265 Song CE. Yang JW. Ha HJ. Lee S. Tetrahedron: Asymmetry  1996,  7:  645 
  CrossrefGoogle Scholar
• 266 Petri A. Pini D. Salvadori P. Tetrahedron Lett.  1995,  36:  1549 
  CrossrefGoogle Scholar
• 267 Pini D. Petri A. Salvadori P. Tetrahedron  1994,  50:  11321 
  CrossrefGoogle Scholar
• 268 Lohray BB. Nandanan E. Bhushan V. Tetrahedron: Asymmetry  1996,  7:  2805 
  CrossrefGoogle Scholar
• 269 Yamashita T. Yasueda H. Nakatani N. Nakamura N. Bull. Chem. Soc. Jpn.  1978,  51:  1183 
  Google Scholar
• 270 Pini D. Petri A. Salvadori P. Tetrahedron: Asymmetry  1993,  4:  2351 
  CrossrefGoogle Scholar
• 271 Petri A. Pini D. Rapaccini S. Salvadori P. Chirality  1995,  7:  580 
  CrossrefGoogle Scholar
• 272 Mandli A. Pini D. Agostini A. Salvadori P. Tetrahedron: Asymmetry  2000,  11:  4039 
  CrossrefGoogle Scholar
• 273 Alvarez R. Hourdin M.-A. Cave C. d’Angelo J. Chaminade P. Tetrahedron Lett.  1999,  40:  7091 
  CrossrefGoogle Scholar
• 274 Cinchilla R. Mazón P. Nájera C. Tetrahedron: Asymmetry  2000,  11:  3277 
  CrossrefGoogle Scholar
• 275 Song CE. Yang JW. Ha HJ. Tetrahedron: Asymmetry  1997,  8:  841 
  CrossrefGoogle Scholar
• 276 Song CE, and Yang JW. inventors; US Patent  5,968,867. 
• 277 Song CE. Oh CR. Lee SW. Lee S. Canali L. Sherrington DC. Chem. Commun.  1998,  2435 
  CrossrefGoogle Scholar
• 278 Bolm C. Maischak A. Gerlach A. Chem. Commun.  1997,  2353 
  CrossrefGoogle Scholar
• 279 Han H. Janda KD. J. Am. Chem. Soc.  1996,  118:  7632 
  CrossrefGoogle Scholar
• 280 Han H. Janda KD. Tetrahedron Lett.  1997,  38:  1527 
  CrossrefGoogle Scholar
• 281 Bolm C. Gerlach A. Angew. Chem., Int. Ed. Engl.  1997,  36:  741 
  Google Scholar
• 282 Han H. Janda KD. Angew. Chem., Int. Ed. Engl.  1997,  36:  1731 
  CrossrefGoogle Scholar
• 283 Salvadori P. Pini D. Petri A. J. Am. Chem. Soc.  1997,  119:  6929 
  CrossrefGoogle Scholar
• 284 Beamer RL. Lawson WW. J. Pharm. Sci.  1966,  55:  53 
  Google Scholar
• 285 Porter MJ. Skidmore J. Chem. Commun.  2000,  1215 
  CrossrefGoogle Scholar
• 286 Baba N. Oda J. Kawaguchi M. Agric. Biol. Chem.  1986,  50:  3113 
  Google Scholar
• 287 Oku M. Arai S. Katayama K. Shioiri T. Synlett  2000,  493 
  Article in Thieme ConnectGoogle Scholar

Lygo, B.; To, D. C. M. Tetrahedron Lett. 2001, submitted.

Cahard, D.; Audouard, C.; Plaquevent, J.-C.; Roques, N. Org. Lett. 2001, submitted.