Highly enantio- and diastereoselective reductive aldol reactions catalyzed by chiral spiro bisphosphine oxides

doi:10.1016/S1872-2067(14)60241-2

Abstract

Abstract:

A spiro bisphosphine oxide (SpinPO) was found to be an efficient chiral Lewis base catalyst in asymmetric reductive aldol reaction of enones and aldehydes in the presence of trichlorosilane as the reductant, affording a variety of β-hydroxyketones in good yields with moderate to high levels of diastereo- and enantioselectivities.

Key words: Aldehyde, Asymmetric catalysis, Enone, Lewis base, Reductive aldol reaction, Spiro bisphosphine oxide

Panke Zhang, Jiawang Liu, Zheng Wang, Kuiling Ding. Highly enantio- and diastereoselective reductive aldol reactions catalyzed by chiral spiro bisphosphine oxides[J]. Chinese Journal of Catalysis, 2015, 36(1): 100-105.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60241-2

https://www.cjcatal.com/EN/Y2015/V36/I1/100

References

[1] Nishiyama H, Shiomi T. Top Curr Chem, 2007, 279: 105
[2] Revis A, Hilty T K. Tetrahedron Lett, 1987, 28: 4809
[3] Matsuda I, Takahashi K, Sato S. Tetrahedron Lett, 1990, 31: 5331
[4] Isayama S, Mukaiyama T. Chem Lett, 1989: 2005
[5] Chiu P, Leung S K. Chem Commun, 2004: 2308
[6] Welle A, Diez-Gonzalez S, Tinant B, Nolan S P, Riant O. Org Lett, 2006, 8: 6059
[7] Chrovian C C, Montgomery J. Org Lett, 2007, 9: 537
[8] Miura K, Yamada Y, Tomita M, Hosomi A. Synlett, 2004: 1985
[9] Shibata I, Kato H, Ishida T, Yasuda M, Baba A. Angew Chem Int Ed, 2004, 43: 711
[10] Shibata I, Tsunoi S, Sakabe K, Miyamoto S, Kato H, Nakajima H, Yasuda M, Baba A. Chem Eur J, 2010, 16: 13335
[11] Taylor S J, Morken J P. J Am Chem Soc, 1999, 121: 12202
[12] Jang H Y, Krische M J. Acc Chem Res, 2004, 37: 653
[13] Lam H W, Joensuu P M, Murray G J, Fordyce E A F, Prieto O, Luebbers T. Org Lett, 2006, 8: 3729
[14] Taylor S J, Duffey M O, Morken J P. J Am Chem Soc, 2000, 122: 4528
[15] Zhao C X, Duffey M O, Taylor S J, Morken J P. Org Lett, 2001, 3: 1829
[16] Russell A E, Fuller N O, Taylor S J, Aurriset P, Morken J P. Org Lett, 2004, 6: 2309
[17] Fuller N O, Morken J P. Synlett, 2005, 1459
[18] Nishiyama H, Shiomi T, Tsuchiya Y, Matsuda I. J Am Chem Soc, 2005, 127: 6972
[19] Shiomi T, Nishiyama H. Org Lett, 2007, 9: 1651
[20] Shiomi T, Adachi T, Ito J, Nishiyama H. Org Lett, 2009, 11: 1011
[21] Yang Y F, Shi T, Zhang X H, Tang Z X, Wen Z Y, Quan J M, Wu Y D. Org Biomol Chem, 2011, 9: 5845
[22] Lam H W, Joensuu P M. Org Lett, 2005, 7: 4225
[23] Chuzel O, Deschamp J, Chausteur C, Riant O. Org Lett, 2006, 8: 5943
[24] Deschamp J, Chuzel O, Hannedouche J, Riant O. Angew Chem Int Ed, 2006, 45: 1292
[25] Zhao D B, Oisaki K, Kanai M, Shibasaki M. J Am Chem Soc, 2006, 128: 14440
[26] Lipshutz B H, Amorelli B, Unger J B. J Am Chem Soc, 2008, 130: 14378
[27] Kato M, Oki H, Ogata K, Fukuzawa S. Synlett, 2009: 1299
[28] Deschamp J, Hermant T, Riant O. Tetrahedron, 2012, 68: 3457
[29] Ou J, Wong W T, Chiu P. Org Biomol Chem, 2012, 10: 5971
[30] Sugiura M, Sato N, Kotani S, Nakajima M. Chem Commun, 2008: 4309
[31] Sugiura M, Sato N, Sonoda Y, Kotani S, Nakajima M. Chem Asian J, 2010, 5: 478
[32] Ohmaru Y, Sato N, Mizutani M, Kotani S, Sugiura M, Nakajima M. Org Biomol Chem, 2012, 10: 4562
[33] Osakama K, Sugiura M, Nakajima M, Kotani S. Tetrahedron Lett, 2012, 53: 4199
[34] Denmark S E, Beutner G L. Angew Chem Int Ed, 2008, 47: 1560
[35] Beutner G L, Denmark S E. Angew Chem Int Ed, 2013, 52: 9086
[36] Han Z B, Wang Z, Zhang X M, Ding K L. Sci Sin Chin (韩召斌, 王正, 张绪穆, 丁奎岭. 中国科学: 化学), 2010, 40: 950
[37] Ding K L, Han Z B, Wang Z. Chem Asian J, 2009, 4: 32
[38] Han Z B, Wang Z, Zhang X M, Ding K L. Angew Chem Int Ed, 2009, 48: 5345
[39] Han Z B, Wang Z, Zhang X M, Ding K L. Tetrahedron: Asymmetry, 2010, 21: 1529
[40] Han Z B, Wang Z, Zhang X M, Ding K L. Chin Sci Bull, 2010, 55: 2840
[41] Zhang Y, Han Z B, Li F Y, Ding K L, Zhang A. Chem Commun, 2010, 46: 156
[42] Han Z B, Wang Z, Ding K L. Adv Synth Catal, 2011, 353: 1584
[43] Shang J, Han Z B, Li Y, Wang Z, Ding K L. Chem Commun, 2012, 48: 5172
[44] Liu X, Han Z B, Wang Z, Ding K L. Acta Chim Sin (刘旭, 韩召斌, 王正, 丁奎岭. 化学学报), 2014, 72: 849
[45] Liu X, Han Z B, Wang, Z, Ding K L. Sci China Chem, 2014, 57: 1073
[46] Liu X, Han Z B, Wang Z, Ding K L. Angew Chem Int Ed, 2014, 53: 1978
[47] Xie J H, Zhou Q L. Acta Chim Sin (谢建华, 周其林. 化学学报), 2014, 72: 778
[48] Zhang P K, Han Z B, Wang Z, Ding K L. Angew Chem Int Ed, 2013, 52: 11054
[49] Denmark S E, Winter S B D, Su X P, Wong K T. J Am Chem Soc, 1996, 118: 7404
[50] Denmark S E, Stavenger R A, Winter S B D, Wong K T, Barsanti P A. J Org Chem, 1998, 63: 9517
[51] Denmark S E, Pham S M, Stavenger R A, Su X P, Wong K T, Nishigaichi Y. J Org Chem, 2006, 71: 3904
[52] Denmark S E, Eklov B M, Yao P J, Eastgate M D. J Am Chem Soc, 2009, 131: 11770