Enantioselective Organocatalytic Michael-Wittig-Michael-Michael Reaction: Dichotomous Construction of Pentasubstituted Cyclopentanecarbaldehydes and Pentasubstituted Cyclohexanecarbaldehydes

被引：47
作者：
Hong, Bor-Cherng [1 ]
Nimje, Roshan Y. [1 ]
Lin, Cheng-Wei [1 ]
Liao, Ju-Hsiou [1 ]
机构：
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 06期
关键词：
ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; MULTISUBSTITUTED CYCLOPENTANES; CONTIGUOUS STEREOCENTERS; CONDENSATION REACTION; ALDOL CONDENSATION; DOMINO REACTIONS; HENRY REACTIONS; CASCADE; DERIVATIVES;
D O I：
10.1021/ol1030487
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Michael addition of carbethoxymethylenetriphenylphosphorane (a Wittig reagent) to nitroalkenes, followed by a reaction with ethyl formylformate and cinnamaldehydes, or formaldehyde and cinnamaldehydes, provided the respective pentasubstituted cyclopentanecarbaldehydes bearing a quaternary carbon center and pentasubstituted cyclohexanecarbaldehydes having five contiguous stereocenters with excellent enantioselectivities (up to >99% ee).
引用
收藏
页码：1278 / 1281
页数：4
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