A way to highly enantiomerically enriched aza-Morita-Baylis-Hillman-type products

被引：137

作者：

Utsumi, Naoto

Zhang, Haile

Tanaka, Fujie

Barbas, Carlos F., III

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 11期

关键词：

aldehydes; asymmetric synthesis; enamines; imines; organocatalysis;

D O I：

10.1002/anie.200603973

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Going Mannich: Difficult to synthesize β-amino carbonyl compounds bearing α-alkylidene groups have been prepared enantioselectively (up to 99% ee) by reaction of β-substituted α,β-unsaturated aldehydes and α-imino esters in the presence of (S)-proline and imidazole under mild conditions (see scheme, PMP = p-methoxyphenyl). Studies suggest that the reaction mechanism involves a Mannich-type reaction/isomerization sequence. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：1878 / 1880

页数：3

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