Lewis Base Organocatalyzed Enantioselective Hydrosilylation of α-Keto Ketimines

doi:10.1007/s40242-014-3396-4

Abstract

Abstract:

A chiral Lewis base organocatalyzed enantioselective hydrosilylation of α-keto ketimines was investigated. The reactions afforded various enantioenriched α-amino ketones with good yields(up to 95%) in moderate to good enantioselectivities(up to 98% e.e.). Furthermore, one of the products was reduced to a chiral 1,2-amino alcohol. Following cyclization of it with triphosgene generated a cannabinoid receptor 1(CB1) inhibitor with good diastereoselectivity.

Key words: Amino alcohol, Asymmetric catalysis, Hydrosilylation

LIU Lixin, ZHENG Yongsheng, HU Xiaoyan, LIAN Chunxia, YUAN Weicheng, ZHANG Xiaomei. Lewis Base Organocatalyzed Enantioselective Hydrosilylation of α-Keto Ketimines[J]. Chemical Research in Chinese Universities, 2014, 30(2): 235-241.

References

[1] Jakubowski J. A., Winters K. J., Naganuma H., Wallentin L., Cardiovasc. Drug Rev., 2007, 25, 357
[2] Bergman S. A., Anesth. Prog., 1999, 46, 10
[3] Elhawi H., Eini H., Douvdevani A., Byk G. Molecules, 2012, 17, 6784
[4] Peng Q., Warloe T., Berg K., Moan J., Kongshaug M., Giercksky K. E., Nesland J. M., Cancer, 1997, 79, 2282
[5] Holm K. J., Spencer C. M., Drugs, 2000, 59, 1007
[6] Jacobsen E. N., Pfaltz A., Yamamoto H., Eds., Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999
[7] Ed.: Ojima I., Catalytic Asymmetric Synthesis, 2nd Ed., VCH, New York, 2000
[8] Lin G. Q., Li Y. M., Chan A. S. C. Principles and Applications of Asymmetric Synthesis, John Wiley &; Sons Inc., New York, 2001
[9] Zheng Y. Y., Xie P., Xing L. X., Wang J. Y., Li J. Q., Org. Process. Res. Dev., 2012, 16, 1921
[10] Fan X., Song Y. L., Long Y. Q., Org. Process. Res. Dev., 2008, 12, 69
[11] Sakuraba S., Takahashi H., Takeda H., Achiwa K., Chem. Pharm. Bull., 1995, 43, 738
[12] Ookawa A., Soai K., J. Chem. Soc. Perkin Trans. 1, 1987, 1465
[13] Xie J. H., Liu S., Kong W. L., Bai W. J., Wang X. C., Wang L. X., Zhou Q. L. J. Am. Chem. Soc., 2009, 131, 4222
[14] Shang G., Liu D., Allen S. E., Yang Q., Zhang X., Chem. Eur. J., 2007, 13, 7780
[15] Ager D. J., Prakash I., Schaad D. R., Chem. Rev., 1996, 96, 835
[16] Bergmeier S. C., Tetrahedron, 2000, 56, 2561
[17] Diekema D. J., Jones R. N. Lancet, 2001, 358, 1975
[18] Hutchinson D. K., Curr. Top. Med. Chem., 2003, 3, 102
[19] Brickner S. J., Hutchinson D. K., Barbachyn M. R., Manninen P. R., Ulanowicz D. A., Garmon S. A., Grega K. C., Hendges S. K., Toops D. S., Ford C. W., Zurenko G. E., J. Med. Chem., 1996, 39, 673
[20] Barbachyn M. R., Hutchinson D. K., Brickner S. J., Cynamon M. H., Kilburn J. O., Klemens S. P., Glickman S. E., Grega K. C., Hendges S. K., Toops D. S., Ford C. W., Zurenko G. E., J. Med. Chem., 1996, 39, 680
[21] Selvakumar N., Srinivas D., Khera M. K., Kumar M. S., Mamidi R. N. V. S., Sarnaik H., Charavaryamath C., Rao B. S., Raheem M. A., Das J., Iqbal J., Rajagopalan R., J. Med. Chem., 2002, 45, 3953
[22] Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Kobayashi J., Akahane S., Akahane M., J. Med. Chem., 2003, 46, 105
[23] Liu H., He X. H., Phillips D., Zhu X. F., Yang K. Y., Lau T., Wu B. G., Xie Y. P., Nguyen T. N., Wang X.(Irmllc), Compounds and Compositions as Inhibitors of Cannatbinoid Receptor 1 Activity, WO 2008/076754, 2008
[24] Zhang Z. G., Synlett., 2008, (12), 1915
[25] Rendler S., Oestreich M., Synthesis, 2005, (11), 1727
[26] Orito Y., Nakajima M., Synthesis, 2006, (9), 1391
[27] Denmark S. E., Beutner G. L., Angew. Chem. Int. Ed., 2008, 47, 1560
[28] Ko?ovský P., Malkov A. V.; Ed.: Dalko P. I., Chiral Lewis Bases as Catalysts In Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007, 255
[29] Kagan H. B. Organocatalytic Enantioselective Reduction of Olefins, Ketones and Imines In Enantioselective Organocatalysis, Ed.: Dalko P. I., Wiley-VCH, Weinheim, 2007, 391
[30] Guizzetti S., Benaglia M., Eur. J. Org. Chem., 2010, 5529
[31] Weickgenannt A., Oestreich M., Chem. Cat. Chem., 2011, 3, 1527
[32] Jones S., Warner C. J. A., Org. Biomol. Chem., 2012, 10, 2189
[33] Malkov A. V., Vranková K., Ston?ius S., Ko?ovský P., J. Org. Chem., 2009, 74, 5839
[34] Malkov A. V., Ston?ius S., Vranková K., Arndt M., Ko?ovský P., Chem. Eur. J., 2008, 14, 8082
[35] Malkov A. V., Ston?ius S., Ko?ovský P., Angew. Chem. Int. Ed., 2007, 46, 3722
[36] Malkov A. V., Liddon A. J. P. S., Ramirez-Lopez P., Bendova L., Haigh D., Ko?ovský P., Angew. Chem., Int. Ed., 2006, 45, 1432
[37] Xiao Y. C., Wang C., Yao Y., Sun J., Chen Y. C., Angew. Chem., Int. Ed., 2011, 50, 10661
[38] Wu X. J., Li Y., Wang C., Zhou L., Lu X. X., Sun J., Chem. Eur. J., 2011, 17, 2846
[39] Pei D., Zhang Y., Wei S. Y., Wang M., Sun J., Adv. Synth. Catal., 2008, 350, 619
[40] Zhou L., Wang Z., Wei S., Sun J., Chem. Commun., 2007, 2977
[41] Pei D., Wang Z. Y., Wei S. Y., Zhang Y., Sun J., Org. Lett., 2006, 8, 5913
[42] Onomura O., Kouchi Y., Iwasaki F., Matsumura Y., Tetrahedron Lett., 2006, 47, 3751
[43] Guizzetti S., Benaglia M., Bonsignore M., Raimondi L., Org. Biomol. Chem., 2011, 9, 739
[44] Guizzetti S., Benaglia M., Rossi S., Org. Lett., 2009, 11, 2928
[45] Sugiura M., Kumahara M., Nakajima M., Chem. Commun., 2009, 3585
[46] Chen X., Hu X. Y., Shu C., Zhang Y. H., Zheng Y. S., Jiang Y., Yuan W. C., Liu B., Zhang X. M., Org. Biomol. Chem., 2013, 11, 3089
[47] Zheng Y. S., Xue Z. Y., Liu L. X., Shu C., Yuan W. C., Zhang X. M., Org. Biomol. Chem., 2013, 11, 412
[48] Xue Z. Y., Liu L. X., Jiang Y., Yuan W. C., Zhang X. M., Eur. J. Org. Chem., 2012, 251
[49] Jiang Y., Chen X., Zheng Y. S., Xue Z. Y., Shu C., Yuan W. C., Zhang X. M., Angew. Chem., Int. Ed., 2011, 50, 7304
[50] Chen X., Zheng Y. S., Shu C., Yuan W. C., Liu B., Zhang X. M., J. Org. Chem., 2011, 76, 9109
[51] Zheng H. J., Chen W. B., Wu Z. J., Deng J. G., Lin W. Q., Yuan W. C., Zhang X. M., Chem. Eur. J., 2008, 14, 9864
[52] Xue Z. Y., Jiang Y., Peng X. Z., Yuan W. C., Zhang X. M., Adv. Synth. Catal., 2010, 352, 2132
[53] Xue Z. Y., Jiang Y., Yuan W. C., Zhang X. M., Eur. J. Org. Chem., 2010, 616
[54] Zheng H. J., Deng J. G., Lin W. Q., Zhang X. M., Tetrahedron Lett., 2007, 48, 7934
[55] Cao X., Jin F., Li Y., Chen, W.; Duan X., Yang L., New J. Chem., 2009, 33, 1578
[56] Babudri F., Fiandanese V., Marchese G., Punzi A., Tetrahedron Lett., 1995, 36, 7305
[57] Dallos T., Hamburger M., Baumgarten M., Org. Lett., 2011, 13, 1936
[58] Charrier J., Landreau C., Deniaud D., Reliquet F., Reliquet A., Meslin J., Tetrahedron, 2001, 57, 4195
[59] Alcaide B., Leon-Santiago M., Perez-Ossorio R., Plumet J., Sierra M., Torre M., Synthesis, 1982, 11, 989
[60] Shibata I., Moriuchi-Kawakami T., Tanizawa D., Suwa T., Sugiyama E., Matsuda H., Baba A., J. Org. Chem., 1998, 63, 383