Dynamic Kinetic Asymmetric Synthesis of Five Contiguous Stereogenic Centers by Sequential Organocatalytic Stetter and Michael-Aldol Reaction: Enantioselective Synthesis of Fully Substituted Cyclopentanols Bearing a Quaternary Stereocenter

被引：52

作者：

Hong, Bor-Cherng ^{[1
]}

Dange, Nitin S. ^{[1
]}

Hsu, Che-Sheng ^{[1
]}

Liao, Ju-Hsiou ^{[1
]}

Lee, Gene-Hsiang ^{[2
]}

机构：

[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 106, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 06期

关键词：

ALDEHYDES;

D O I：

10.1021/ol200006e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of fully substituted cyclopentanes bearing a quaternary carbon center and five contiguous stereogenic centers has been achieved by sequential organocatalyzed Stetter and Michael Aldol reactions of heteroaromatic aldehydes, nitroalkenes, and alpha,beta-unsaturated aldehydes via the [1 + 2 + 2] annulation strategy with dynamic kinetic asymmetric transformation and excellent enantioselectivities (up to > 99% ee).

引用

收藏

页码：1338 / 1341

页数：4

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