Sterically and electronically tunable and bifunctional organocatalysts: Design and application in asymmetric aldol reaction of cyclic ketones with aldehydes

被引：110

作者：

Chen, Jia-Rong ^{[1
]}

Li, Xin-Yong ^{[1
]}

Xing, Xiao-Ning ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Key lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 21期

关键词：

D O I：

10.1021/jo0615089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterically and electronically tunable and bifunctional organocatalysts have been developed and evaluated in the direct aldol reaction of heterocyclic ketones. Catalysts with different substituents showed variable catalytic efficiency for analogous substrates, indicating the importance of fine-tuning the strength of the hydrogen bonding in the two NH groups. The reactions all proceeded in good to high yield and with excellent enantioselectivities ranging from 90% to > 99% ee. In most cases, high diastereoselectivities ranging from 96/4 to 99/1 were obtained for the anti aldol adduct.

引用

页码：8198 / 8202

页数：5

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