Highly Enantioselective Michael Addition of α-Substituted Cyano Ketones to β,γ-Unsaturated α-Keto Esters using Bifunctional Thiourea-Tertiary Amine Catalysts: An Easy Access to Chiral Dihydropyrans

被引：67

作者：

Zhao, Sheng-Li ^{[1
]}

Zheng, Chang-Wu ^{[1
]}

Wang, Hai-Feng ^{[1
]}

Zhao, Gang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期

基金：

中国国家自然科学基金;

关键词：

enantioseteroselectivity; Michael addition; organocatalysts; thioureas; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; DERIVATIVES; ORGANOCATALYSTS; CONSTRUCTION; NITROALKENE; ENAMINES; MALONATE; SPECTRA; UREA;

D O I：

10.1002/adsc.200900516

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An asymmetric Michael addition of alpha-substituted cyano ketones to beta,gamma-unsaturated alpha-keto esters to form chiral dihydropyrans catalyzed by a series of alpha-amino acid-derived thiourea-tertiary amines is presented. A novel tyrosine-derived thiourea catalyst was identified as the optimal catalyst providing the desired product in 91-95% yields and with 90-96% ee at a low catalyst loading of 2.0 mol%. The utility of the reaction was exemplified by facile conversion of the dihydropyran product into pharmaceutically useful dihydropyridine.

引用

页码：2811 / 2816

页数：6

共 53 条

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