Diastereoselective and Enantioselective Michael Addition Reactions of Ketones and Aldehydes to Nitro Olefins Catalyzed by C2-Symmetric Axially-Unfixed Biaryl-Based Organocatalysts Derived from Enantiopure α-Proline

被引：26

作者：

Zhao, Hong-Wu ^{[1
]}

Li, Hai-Long ^{[1
]}

Yue, Yuan-Yuan ^{[1
]}

Sheng, Zhui-Hui ^{[1
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 09期

关键词：

Synthetic methods; C-C coupling; Organocatalysis; Michael addition; Nitrogen heterocycles; Enantioselectivity; Diastereoselectivity; ASYMMETRIC ALDOL REACTIONS; CYCLIC-KETONES; BIFUNCTIONAL ORGANOCATALYSTS; PYRROLIDINE; BACKBONE; DESIGN;

D O I：

10.1002/ejoc.201201306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of axially-unfixed biaryl-based pyrrolidines with C-2-symmetry were designed and synthesized by using enantiopure alpha-proline as a chiral source. These bifunctional organocatalys provided Michael adducts in high chemical yields (up to 99%) and with excellent stereoselectivities (up to 99: 1 dr and 96% ee) in the direct Michael addition reactions of a variety of ketones and aldehydes to nitro olefins. The transition states were proposed to clarify the stereochemical course of the examined reactions.

引用

页码：1740 / 1748

页数：9

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