The combination of domino process and kinetic resolution: organocatalytic synthesis of functionalised cyclopentenes by sequential SN2′-Michael reaction

被引：31

作者：

Yeh, Lun Fu ^{[1
]}

Anwar, Shaik ^{[1
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

TETRAHEDRON | 2012年 / 68卷 / 36期

关键词：

Kinetic resolution; Organocatalysis; Cascade; Michael reaction; Cyclopentene; MICHAEL-ALDOL CONDENSATION; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; NITROALLYLIC ACETATES; ALCOHOLS; CONSTRUCTION; 1,2-DIOLS; KETONES; ENALS;

D O I：

10.1016/j.tet.2012.06.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S(N)2'-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee). (C) 2012 Published by Elsevier Ltd.

引用

页码：7317 / 7321

页数：5

共 24 条

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