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One-pot synthesis of oxazolines and application to the cyanosilylation of prochiral aldehydes

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Abstract

A new class of modular functionalized d-oxazoline ligands, 6a–6b, 7a, 8(a–d), and 9(a–d) have been synthesized by use of a simple, one-pot method under inert moisture-free conditions. Product structures were fully characterized by use of NMR and IR spectroscopy and MS. The compounds were found to be highly active catalysts for cyanosilylation of prochiral benzaldehyde (50–96 % yield).

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References

  1. J.A. Frump, Chem. Rev. 71, 483–505 (1971)

    Article  CAS  Google Scholar 

  2. A.K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron 9, 1–45 (1998)

    Article  CAS  Google Scholar 

  3. A. Pfaltz, Heterocycl. Chem. 36, 1437–1451 (1999)

    Article  CAS  Google Scholar 

  4. A. Pfaltz, Acc. Chem. Res. 26, 339–345 (1993)

    Article  CAS  Google Scholar 

  5. M.P. Doyle, M.N. Protopova, Tetrahedron 54, 1946–7919 (1998)

    Article  Google Scholar 

  6. A.I.J. Meyers, Heterocycl. Chem. 35, 991–1002 (1998)

    Article  CAS  Google Scholar 

  7. A.I. Meyers, A.J. Price, Org. Chem. 63, 412–413 (1998)

    Article  CAS  Google Scholar 

  8. T.G. Gant, A.I. Meyers, Tetrahedron 50, 2297–2360 (1994)

    Article  CAS  Google Scholar 

  9. O. Reiser, Nachr. Chem. Technol. Lab. 44, 744–750 (1996)

    Article  CAS  Google Scholar 

  10. C. Bolm, Angew. Chem. 103, 556–558 (1991)

    Article  CAS  Google Scholar 

  11. R.E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 31, 6005–6008 (1990)

    Article  CAS  Google Scholar 

  12. R.E. Lowenthal, S. Masamune, Tetrahedron Lett. 32, 7373–7376 (1991)

    Article  CAS  Google Scholar 

  13. D.A. Evans, K.A. Woerpel, M.M. Hinman, M.M.J. Faul, Am. Chem. Soc. 113, 726–728 (1991)

    Article  CAS  Google Scholar 

  14. A.V. Bedekar, P.G. Andersson, Tetrahedron Lett. 37, 4073–4076 (1996)

    Article  CAS  Google Scholar 

  15. A.V. Bedekar, E.B. Koroleva, P.G.J. Andersson, Org. Chem. 62, 2518–2526 (1997)

    Article  CAS  Google Scholar 

  16. R. Boulch, A. Scheurer, P. Mosset, R.W. Saalfrank, Tetrahedron Lett. 41, 1023–1026 (2000)

    Article  CAS  Google Scholar 

  17. D.A. Evans, M.M. Faul, M.T. Bilodeau, B.A. Anderson, D.M.J. Barnes, Am. Chem. Soc. 115, 5328–5329 (1993)

    Article  CAS  Google Scholar 

  18. E.J. Corey, K. Ishihara, Tetrahedron Lett. 33, 6807–6810 (1992)

    Article  CAS  Google Scholar 

  19. D.A. Evans, S.J. Miller, T. Lectka, P.J. von Matt, Am. Chem. Soc. 121, 7559–7573 (1999)

    Article  CAS  Google Scholar 

  20. D.A. Evans, D.M. Barnes, J.S. Johnson, T. Lectka, S.J. Miller, J.A. Murry, R.D. Norcross, E.A. Shaughnessy, K.R.J. Campos, Am. Chem. Soc. 121, 7482–7594 (1999)

    Google Scholar 

  21. D.A. Evans, E.J. Olhava, J.S. Johnson, J.M. Janey, Angew. Chem. 110, 3554–3557 (1998)

    Google Scholar 

  22. M. Johannsen, K.A.J. Jørgensen, Org. Chem. 60, 5757–5762 (1995)

    Article  CAS  Google Scholar 

  23. M. Johannsen, K.A. Jørgensen, Tetrahedron 52, 7321–7328 (1996)

    Article  CAS  Google Scholar 

  24. D.A. Evans, M.C. Kozlowski, J.A. Murry, C.S. Burgey, K.R. Campos, B.T. Connell, R.J.J. Staples, Am. Chem. Soc. 121, 669–685 (1999)

    Article  CAS  Google Scholar 

  25. D.A. Evans, C.S. Burgey, M.C. Kozlowski, S.W.J. Tregay, Am. Chem. Soc. 121, 686–699 (1999)

    Article  CAS  Google Scholar 

  26. N. End, A. Pfaltz, Chem. Commun. 5, 589–590 (1998)

    Article  Google Scholar 

  27. N. End, L. Macko, M. Zehnder, A. Pfaltz, Chem. Eur. J. 4, 818–824 (1998)

    Article  CAS  Google Scholar 

  28. K. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 74, 232–240 (1991)

    Article  Google Scholar 

  29. H. Nishiyama, S. Yamaguchi, S.-B. Park, K. Itoh, Tetrahedron 4, 143–150 (1993)

    Article  CAS  Google Scholar 

  30. H. Hishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, K. Itoh, Organometallics 8, 846–848 (1989)

    Article  Google Scholar 

  31. Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, Tetrahedron 7, 2453–2462 (1996)

    Article  CAS  Google Scholar 

  32. S. Lee, C.W. Lim, C.E. Song, I.O. Kim, C. Jun, Tetrahedron 8, 2927–2932 (1997)

    Article  CAS  Google Scholar 

  33. A.S. Gokhale, A.B.E. Minidis, A. Pfaltz, Tetrahedron Lett. 36, 1831–1834 (1995)

    Article  CAS  Google Scholar 

  34. M.B. Andrus, A.B. Argade, X. Chen, M.G. Pamment, Tetrahedron Lett. 36, 2945–2948 (1995)

    Article  CAS  Google Scholar 

  35. J.J. Miller, S. Rajaram, C. Pfaffenroth, M.S. Sigman, Tetrahedron 65, 3110 (2009)

    Article  CAS  Google Scholar 

  36. S. Barroso, G. Blay, L. Al-Midfa, M. Carmen, M.C. Munoz, R.P. Jose, J. Org. Chem. 73, 6389 (2008)

    Article  CAS  Google Scholar 

  37. S. Barroso, G.B. Pedro, Org. Lett. 2007, 9 (1983)

    Google Scholar 

  38. G. Chollet, M.-G. Guillerez, E. Schulz, Chem. Eur. J. 13, 992 (2007)

    Article  CAS  Google Scholar 

  39. D. Carmona, C. Vega, N. Garcia, F.J. Lahoz, S. Elipe, L.A. Oro, M.P. Lamata, F. Viguri, R. Borao, Organometallics 25, 1592 (2006)

    Article  CAS  Google Scholar 

  40. W.B. Zhang, F. Xie, H. Yoshinaga, T. Kida, Y. Nakatsuji, I. Ikeda, Synlett 8, 1185–1188 (2006)

    Article  Google Scholar 

  41. Y. Bunya, T. Sengoku, Y. Imamura, Y. Arai, Heterocycles 76, 833 (2008)

    Article  CAS  Google Scholar 

  42. T.N. Le, Q.P.B. Nguyen, J.N. Kim, T.H. Kim, Tetrahedron Lett. 48, 7834 (2007)

    Article  CAS  Google Scholar 

  43. D.L. Liu, F. Xie, W.B.J. Zhang, Org. Chem. 72, 6992 (2007)

    Article  CAS  Google Scholar 

  44. R.P.J. Bronger, P.J. Guiry, Tetrahedron 2007, 18 (1094)

    Google Scholar 

  45. B. Ganchegui, C. Chevrin, S. Bouquillon, J. Le Bras, F. Henin, J. Muzart, Phosphorus, Sulfur Silicon Relat. Elem. 181, 2635 (2006)

    Article  CAS  Google Scholar 

  46. A.L. Braga, D.S. Luedtke, J.A. Sehnem, E.E. Alberto, Tetrahedron 61, 11664 (2005)

    Article  CAS  Google Scholar 

  47. J.M. Fraile, J.I. Garcia, A. Gissibl, A.M. Jose, J.A.E. Pires, O. Reiser, M. Roldan, I. Villalba, Chem. Eur. J. 13, 8830 (2007)

    Article  CAS  Google Scholar 

  48. Y. Ito, M. Sawamura, T.J. Hayashi, Am. Chem. Soc. 108, 6405 (1986)

    Article  CAS  Google Scholar 

  49. E.J. Le, B.L. Pagenkopf, Eur. J. Org. Chem. 35, 6109 (2009)

    Google Scholar 

  50. M. Mizuno, H. Inoue, T. Naito, L. Zhou, H. Nishiyama, Chem. Eur. J. 15, 8985 (2009)

    Article  CAS  Google Scholar 

  51. S. Doherty, J.G. Knight, A. McRae, W.H. Ross, W. Clegg, Eur. J. Org. Chem. 10, 1759 (2008)

    Article  Google Scholar 

  52. H. Hnoue, M. Kikuchi, J.-I. Ito, H. Nishiyama, Tetrahedron 64, 493 (2008)

    Article  Google Scholar 

  53. L. Mei, Y. Hao, J.H. Zhang, K.L. Hu, W.M. Pang, Res. Chem. Intermed. 35, 123 (2009)

    Article  CAS  Google Scholar 

  54. M.J. Oila, E.T. Jan, A.M.P. Koskinen, Lett. Org. Chem. 5, 11 (2008)

    Article  CAS  Google Scholar 

  55. S.K. Ginotra, V.K. Singh, Org. Biomol. Chem. 5, 3932 (2007)

    Article  CAS  Google Scholar 

  56. D.A. Evans, D. Seidel, M. Rueping, H.W. Lam, J.T. Shaw, C.W.J. Downey, Am. Chem. Soc. 125, 12692 (2003)

    Article  CAS  Google Scholar 

  57. R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Org. Lett. 8, 6099 (2006)

    Article  CAS  Google Scholar 

  58. A.I. Meyers, J.J. Slade, Org. Chem. 45, 2785 (1980)

    Article  CAS  Google Scholar 

  59. J.E. Dubois, C.C.R. Lion, Hebd. Seances Acad. Sci. 274, 303 (1972)

    CAS  Google Scholar 

  60. H. Vorbrüggen, K. Krolikiewicz, Tetrahedron 49, 9353 (1993)

    Article  Google Scholar 

  61. A. Cwik, Z. Hell, A. Hegedüs, Z. Finta, Z. Horvath, Tetrahedron Lett. 43, 3985 (2002)

    Article  CAS  Google Scholar 

  62. J.S. Panek, C.E.J. Masse, Org. Chem. 63, 2382 (1998)

    Article  CAS  Google Scholar 

  63. K. Kamata, I. Agata, A.I.J. Meyers, Org. Chem. 63, 3113 (1998)

    Article  CAS  Google Scholar 

  64. B. Oussaid, J. Berlan, M. Soufiaoui, B. Garrigues, Synth. Commun. 25, 659 (1995)

    Article  CAS  Google Scholar 

  65. C. Bolm, K. Weickhardt, M. Zehnder, T. Ranff, Chem. Ber. 124, 1173 (1991)

    Article  CAS  Google Scholar 

  66. D.P. Schumacher, J.E. Clark, B.L. Murphy, P.A.J. Fischer, Org. Chem. 55, 5291 (1990)

    Article  CAS  Google Scholar 

  67. J.F. Bower, C.J. Martin, D.J. Rawson, A.M.Z. Slawin, J.M.J. Williams, J. Chem. Soc., Perkin Trans. 1, 333 (1996)

    Article  Google Scholar 

  68. H. Witte, W. Seeliger, Angew. Chem. Int. Ed. Engl. 11(4), 287 (1972)

    Article  CAS  Google Scholar 

  69. J.F. Yu, T.V. RajanBabu, J.R. Parquette, J. Am. Chem. Soc. 130, 7845 (2008)

    Article  CAS  Google Scholar 

  70. S. Doherty, J.G. Knight, A. McRae, R.W. Harrington, W. Clegg, J. Org. Chem. 10, 1759 (2008)

    Google Scholar 

  71. G.C. Hargaden, H. Muller-Bunz, P.J. Guiry, Eur. J. Org. Chem. 25, 4235 (2007)

    Article  Google Scholar 

  72. H.A. McManus, P.J.J. Guiry, Org. Chem. 67, 8566 (2002)

    Article  CAS  Google Scholar 

  73. M. Gomez, S. Jansat, G. Muller, G. Aullon, M.A. Maestro, Eur. J. Inorg. Chem. 21, 4341 (2005)

    Article  Google Scholar 

  74. A.S. Gajare, N.S. Shaikh, G.K. Jnaneshwara, V.H. Deshpande, T. Ravindranathan, A.V. Bedekar, Perkin 1 6, 999 (2000)

    Article  Google Scholar 

  75. M. Luo, J.H. Zhang, J. Sun, S.M. Zhou, H. Yin, K.L.J. Hu, Comb. Chem. 11, 220 (2009)

    Article  Google Scholar 

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Acknowledgments

This work was supported by Hefei University of Technology. The authors acknowledge the University of Science and Technology of China for spectral measurements.

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Authors and Affiliations

  1. Department of Chemical Engineering, Hefei University of Technology, Hefei, 230009, Anhui, China

    M. Luo

  2. Chemical Engineering, Shandong University, Jinan, 250100, China

    B. Yan

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  1. M. Luo
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Correspondence to M. Luo.

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Luo, M., Yan, B. One-pot synthesis of oxazolines and application to the cyanosilylation of prochiral aldehydes. Res Chem Intermed 41, 1171–1180 (2015). https://doi.org/10.1007/s11164-013-1262-5

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