Research Progress on Nitroso-ene Reaction

doi:10.6023/cjoc201207026

Abstract

Nitroso-ene reaction is one of the most efficient methods to construct allylamines which are the versatile building block in synthetic organic chemistry. The reaction has been embedded as the key step in the total synthesis of natural products and pharmaceuticals. This review focuses on the development, application and mechanistic study of nitroso-ene reaction.

Key words: allylamine, nitroso compound, nitroso-ene reaction, natural product synthesis

Cite this article

Huang Shahua, Huo Huaxing, Li Wenhua, Hong Ran. Research Progress on Nitroso-ene Reaction[J]. Chin. J. Org. Chem., 2012, 32(10): 1776-1791.

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References

[1] (a) Meyer, V.; Locher, J. Ber. 1874, 7, 670.

(b) Meyer, V.; Locher, J. Ber. 1874, 7, 1506.

(c) Baeyer, A.; Caro, H. Ber. 1874, 7, 809.

(d) Baeyer, A. Ber. 1874, 7, 1638.

(e) Baeyer, A.; Caro, H. Ber. 1874, 7, 963.

[2] Gowenlock, B. G.; Richter-Addo, G. B. J. Chem. Educ. 2008, 85, 1243

[3] Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, D. D.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464.

[4] Kersten, R. D.; Dorrestein, P. C. Nat. Chem. Biol. 2010, 6, 636

[5] Boyer, J. H. In The Chemistry of the Nitro and Nitroso Groups, Part 1, Ed.: Patai, S., Interscience Publishers, New York, 1969, Chapter 5.

[6] Zuman, P.; Shah, B. Chem. Rev. 1994, 94, 1621.

[7] (a) Wichterle, O. Collect. Czech. Chem. Commun. 1947, 12, 292.

(b) Arbuzov, Y. A. Dokl. Akad. Nauk SSSR 1948, 60, 993.

[8] Lewis, J. W.; Myers, P. L.; Ormerod, J. A. J. Chem. Soc., Perkin Trans. 1 1972, 2521.

[9] Banks, R. E.; Barlow M. G.; Haszeldine, R. N. J. Chem. Soc. 1965, 4714.

[10] For reviews, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.

(b) Senanayake, C. H. Aldrichim. Acta 1998, 31, 3.

(c) Lait, S. M.; Rankic, D. A.; Keay, B. A. Chem. Rev. 2007, 107, 767.

[11] (a) Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 31, 991.

(b) Oppolzer, W.; Tamura, O.; Sundarababu, G.; Signer, M. J. Am. Chem. Soc. 1992, 114, 5900.

(c) Momiyama, N.; Yamamoto, H. Org. Lett. 2002, 4, 3579.

[12] Goelitz, P.; Meijere, A. Angew. Chem. 1977, 89, 892.

[13] (a) Aston, A.; Menard, M. J. Am. Chem. Soc. 1935, 57, 1922.

(b) Forrester, A. R.; Hepburn, S. P. J. Chem. Soc. C 1971, 3322.

(c) Goldman, J. Tetrahedron 1973, 29, 3833.

[14] Druellinger, M. L. J. Heterocycl. Chem. 1976, 13, 1001.

[15] (a) Adam, W.; Bottle, S. E.; Peters, K. Tetrahedron Lett. 1991, 32, 4283.

(b) Torssell, K. Tetrahedron 1970, 26, 2759.

(c) Forrester, A. R.; Henderson, J.; Reid, K. Tetrahedron Lett. 1983, 24, 5547.

[16] (a) Ginsburg, V. A. J. Org. Chem. USSR (Engl. Trans.) 1974, 10, 1427.

(b) Barr, A.; Hazeldine, R. N. J. Chem. Soc. 1955, 1881.

[17] (a) Lin, C.-T.; Hsu, W.-J. Can. J. Chem. 1989, 67, 2153.

(b) Viehe, H. G.; Merenyi, R.; Francotte, E.; Van Meerssche, M.; Germain, G.; Declercq, J. P.; Bodart-Gilmont, J. J. Am. Chem. Soc. 1977, 99, 2340.

(c) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 12, 1173.

(d) Christie, C. C.; Kirby, G. W.; McGuian, H.; Mackinnon, J. W. M. J. Chem. Soc., Perkin. Trans. 1 1985, 1972.

[18] (a) Knight, G. T. J. Chem. Soc., Chem. Commun. 1970, 1016.

(b) Johannsen, M.; Jùrgensen, K. A. Chem. Rev. 1998, 98, 1689.

[19] (a) Glaser, R.; Murmann, R. K.; Barnes, C. L. J. Org. Chem. 1996, 61, 1047.

b) Stowell, J. C. J. Org. Chem. 1971, 36, 3055.

(c) Yamamoto, H.; Momiyama, N. J. Chem. Soc., Chem. Commun. 2005, 3514.

[20] (a) Miller, M. J.; Bodnar, B. S. Angew. Chem., Int. Ed. 2011, 50, 5630.

(b) Janey, J. M. Angew. Chem., Int. Ed. 2005, 44, 4292.

(c) Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2004, 43, 2995.

(d) Studer, A. Synthesis 1996, 793.

(e) Voget, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1323.

[21] Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3113.

[22] (a) Yamamoto, H.; Kawasaki, M. Bull. Chem. Soc. Jpn. 2007, 80, 595.

(b) Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965.

[23] Guo, H.; Cheng, L.; Cun, L. F.; Gong, L. Z.; Miac, A. G.; Jiang, Y. Z. J. Chem. Soc., Chem. Commun. 2006, 429.

[24] (a) Brown, S. P.; Brochu, M. P.; Sinz C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808.

(b) Yanagisawa, A.; Arai, T. Chem. Commun. 2008, 1165.

[25] Mikami, K.; Shimizsu, M. Chem. Rev. 1992, 92, 1021.

[26] Alder, K.; Pascher, F.; Schimitz, A. Dtsch. Chem. Ges. 1943, 76, 27.

[27] (a) Magnus, P.; Lacour, J.; Goldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087.

(b) Seebach, D.; Overhand, M.; Kuèhnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.

(c) Cole, D. C. Tetrahedron 1994, 50, 9517.

(d) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1.

(e) Burgess, K.; Liu, L.; Pal, B. J. Org. Chem. 1993, 58, 4758.

(f) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444.

[28] Banks, R. E.; Barlow, M. G.; Haszeldine, R. N. J. Chem. Soc. 1965, 4714.

[29] Keussler, V.; Luttke, W. Z. Elektrochem. 1959, 63, 614

[30] (a) Corrie, J. E. T.; Kirby, G. W.; Mackinnon, J. W. M. J. Chem. Soc., Perkin Trans. 1 1985, 883.

(b) Quadrelli, P.; Mella, M.; Invernizzi, A. G.; Caramella, P. Tetrahedron 1999, 55, 10497.

(c) Quadrelli, P.; Campari, P.; Mella, M.; Caramella, P. Tetrahedron Lett. 2000, 41, 2019.

[31] Quadrelli, P.; Invernizzi, A. G.; Caramella, P. Tetrahedron Lett. 1996, 37, 1909.

[32] (a) Knight, G. T.; Pepper, B. Tetrahedron 1971, 27, 6201.

(b) Knight, G. T.; Loadman, M. J. R. J. Chem. Soc., B 1971, 2107.

[33] Adam, W.; Krebs, O. Chem. Rev. 2003, 103, 4131.

[34] (a) Corrie, J. E. T.; Kirby, G. W.; Mackinnon, J. W. M. J. Chem. Soc., Perkin Trans. 1 1985, 883.

(b) Kirby, G. W.; McGuigan, H.; McLean, D. J. J. Chem. Soc., Perkin Trans. 1 1985, 1961.

[35] Kirby, G. W. Chem. Soc. Rev. 1977, 6, 12.

[36] Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007.

[37] Ensley, H. E.; Mahadevan, S. Tetrahedron Lett. 1989, 30, 3255.

[38] (a) Schollkopf, U; Tonne, P.; Schafer, H.; Markusch, P. Ann. Chem. 1969, 722, 45.

(b) Schollkopf, U; Tonne, P. Ann. Chem. 1971, 753, 135.

[39] (a) O’Bannon, P. E.; Dailey, W. P. Tetrahedron Lett. 1988, 29, 987.

(b) O’Bannon, P. E.; Dailey, W. P. Tetrahedron Lett. 1988, 29, 5719.

[40] Quadrelli, P.; Mella, M.; Caramella, P. Tetrahedron Lett. 1998, 39, 3233.

[41] Quadrelli, P.; Mella, M.; Invernizzi, A. G.; Caramella, P. Tetrahedron 1999, 55, 10497.

[42] Adam, W.; Bottke, N.; Krebs, O.; Saha-Moèller, C. R. Eur. J. Org. Chem. 1999, 1963.

[43] Iwasa, S.; Fakhruddin, A.; Tajima, K.; Nishiyama, H. Tetrahedron Lett. 2004, 45, 9323.

[44] Malkov, A. V. Atkinson, D.; Kabeshov, M. A.; Edgar, M. Adv. Synth. Catal. 2011, 353, 3347.

[45] Read de Alaniz, J.; Frazier, C. P.; Engelking, J. R. J. Am. Chem. Soc. 2011, 133, 10430.

[46] Read de Alaniz, J.; Frazier, C. P.; Engelking, J. R. Org. Lett. 2012, 14, 3620.

[47] Lu, C-D.; Tusun, X. Synlett 2012, 1801.

[48] (a) Johannsen, M.; Jùrgensen, K. A. J. Org. Chem. 1994, 59, 214. (b) Johannsen, M.; Jùrgensen, K. A. J. Org. Chem. 1995, 60, 5979. (c) Srivastava, R. S.; Nicholas, K. M. J. Am. Chem. Soc. 1996, 118, 3311.

(d) Srivastava, R. S.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 3302.

(e) Srivastava, R. S.; Nicholas, K. M. J. Org. Chem. 1994, 59, 5365.

(f) Mùller, E. R.; Jùrgensen, K. A. J. Am. Chem. Soc. 1993, 115, 11814.

(g) Ho, C.-M.; Lau, T.-C. Chem. Commun. 2000, 24, 859.

(h) Hogan, G. A.; Gallo, A. A.; Nicholas, K. M.; Srivastava, R. S. Tetrahedron Lett. 2002, 43, 9505.

(i) Srivastava, R. S. Tetrahedron Lett. 2003, 44, 3271.

[49] Sharpless, K. B. J. Am. Chem. Soc. 1978, 100, 7061.

[50] (a) Cenini, S. Ragaini, F.; Tollari, S.; Paone D. J. Am. Chem. Soc. 1996, 118, 11964.

(b) Srivastava, R. S.; Kolel-Veetil, M. K.; Nicholas, K. M. Tetrahedron Lett. 2002, 43, 931.

[51] Merisor, E.; Conrad, J.; Klaiber, I.; Mika, S.; Beifuss, U. Angew. Chem., Int. Ed. 2007, 46, 3353.

[52] Merisor, E.; Conrad, J.; Klaiber, I.; Mika, S.; Beifuss, U. Synlett 2010, 1766.

[53] Roberts, J. S.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1972, 328.

[54] Solomon, D. H.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 1981, 22, 1165.

[55] Haszeldine, R. N.; Barlow, M. G.; Murria, K. W. J. Chem. Soc., Perkin Trans. 1 1980, 1960.

[56] Schenk, C.; De Boer, T. J. Tetrahedron 1979, 35, 147.

[57] Miller, M. J.; Yang, B. Tetrahedron Lett. 2010, 51, 328.

[58] Keck, G. E.; Webb, R. R. J. Am. Chem. Soc. 1981, 103, 3174.

[59] (a) Goodwin, S.; Shoolery, J. N.; Horning, E. C. J. Am. Chem. Soc. 1959, 81, 3736.

(b) Okamoto, T.; Torii, A.; Isogai, Y. Chem. Pharm. Bull. 1968, 16, 1860.

(c) Wildman, W. C.; Bailey, D. T. J. Org. Chem. 1968, 33, 3749.

(d) Wildman, W. C.; Bailey, D. T. J. Am. Chem. Soc. 1970, 92, 5538.

[60] Martin, S. F.; Puckette, T. A.; Colapret, J. A. J. Org. Chem. 1979, 44, 3391.

[61] Wijnberg, J. B. P. A.; Speckamp, W. N. Tetrahedron 1978, 34, 2579.

[62] (a) Matsumura, Y.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3249.

(b) Matsumura, Y.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2004, 6, 965.

[63] Clive, D. L. J.; Yu, M.; Wang, J.; Yeh, V. S. C.; Kang, S. Chem. Rev. 2005, 105, 4483

[64] Vasella, A.; Zhang, F. Helv. Chim. Acta 2007, 90, 2315.

[65] Vasella, A.; Zhang, F. Helv. Chim. Acta 2008, 91, 2351.

[66] Fokin, A. A.; Yurchenko, A. G.; Rodionov, V. N.; Gunchenko, P. A.; Yurchenko, R. I.; Reichenberg, A.; Wiesner, J.; Hintz, M.; Jomaa, H.; Schreiner, P. R. Org. Lett. 2007, 9, 4379.

[67] Haley, M. M.; Jeffrey, J. L.; McClintock, S. P. J. Org. Chem. 2008, 73, 3288.

[68] Murru, S.; Gallo, A. A.; Srivastava, R. S. J. Org. Chem. 2012, 77, 7119.

[69] Hamer, J.; Macaluso, A. Tetrahedron Lett. 1963, 4, 381.

[70] Seymour, C. A.; Greene, F. D. J. Org. Chem. 1982, 47, 5226.

[71] Davies, A. G.; Schiesser, C. H. Tetrahedron 1991, 47, 1707.

[72] Adam, W.; Krebs, O. J. Org. Chem. 2003, 68, 2420.

[73] (a) Leach, A. G.; Houk, K. N. Chem. Commun. 2002, 12, 1243.

(b) Leach, A. G.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 14820.

[74] Leach, A. G.; Houk, K. N. J. Am Chem. Soc. 2003, 125, 13825.

[75] Lu, X. Org. Lett. 2004, 6, 2813.

[76] Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703.

[77] Adam, W.; Bottke, N.; Krebs, O.; Engels, B. J. Am. Chem. Soc. 2001, 123, 5542.

[78] Adam, W.; Bottke, N.; Krebs, O. J. Am. Chem. Soc. 2000, 122, 6791.

[79] Kreae, G.; Felber, H.; Ritter, A.; Ascherl, B.; Vasella, A. Recl. Trav. Chim. Pays-Bas 1986, 105, 295. Adam, W.; Krebs, O. J. Am. Chem. Soc. 2002, 124, 12938.

亚硝基-烯(Nitroso-ene)反应的研究进展