Organocatalytic Michael Addition of Nitro Esters to α,β-Unsaturated Aldehydes: Towards the Enantioselective Synthesis of trans-3-Substituted Proline Derivatives

被引：24

作者：

Han, Man-Yi ^{[1
]}

Zhang, Yong ^{[2
]}

Wang, Huai-Zhen ^{[1
]}

An, Wan-Kai ^{[1
]}

Ma, Bao-Chun ^{[1
]}

Zhang, Yuan ^{[1
]}

Wang, Wei ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Gannan Normal Univ, Coll Chem & Chem Engn, Ganzhou 341000, Jiangxi, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期

基金：

中国国家自然科学基金;

关键词：

asymmetric organocatalysis; Michael addition; trans-3-substituted proline derivatives; ASYMMETRIC CONJUGATE ADDITION; PROTEINOGENIC AMINO-ACIDS; 3-SUBSTITUTED PROLINES; SUBSTITUTED PROLINES; DIELS-ALDER; NITROALKANES; NITROACETATE; EQUIVALENTS; CATALYSIS;

D O I：

10.1002/adsc.201200538

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A facile five-step strategy has been developed for the enantioselective synthesis of trans-3-substituted proline derivatives with high diasteroselectivity (dr>20:1) and enantioselectivity (up to 97% ee). The key step is the asymmetric organocatalytic Michael addition of nitro esters to a,beta-unsaturated aldehydes, which affords the chiral Michael adducts in high yields (up to 96%) and excellent enantioselectivity (up to 99% ee) by using diarylprolinol silyl ether as the organocatalyst.

引用

页码：2635 / 2640

页数：6

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