Asymmetric conjugate reduction of α,β-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

被引：125

作者：

Kanazawa, Y ^{[1
]}

Tsuchiya, Y ^{[1
]}

Kobayashi, K ^{[1
]}

Shiomi, T ^{[1
]}

Itoh, J ^{[1
]}

Kikuchi, M ^{[1
]}

Yamamoto, Y ^{[1
]}

Nishiyama, H ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2006年 / 12卷 / 01期

关键词：

asymmetric catalysis; conjugate reduction; hydrosilanes; oxazolines; rhodium;

D O I：

10.1002/chem.200500841

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New asymmetric conjugate reduction of beta,beta-disubstituted alpha,beta-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high en antioselectivity. (E)-4Phenyl-3-penten-2-one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60 degrees C in 95% ee and 98% ee, respectively, by 1 mol% of catalyst loading. (EtO)(2)MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-beta-methylcinnamate and beta-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.

引用

页码：63 / 71

页数：9

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