Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis

被引：251

作者：

Aggarwal, VK ^{[1
]}

Fulford, SY ^{[1
]}

Lloyd-Jones, GC ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 11期

关键词：

asymmetric catalysis; autocatalysis; kinetics; proton transfer; reaction mechanisms;

D O I：

10.1002/anie.200462462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) One step beyond: Proton transfer (step 3, see scheme), not C-C bond formation (step 2) as previously thought, is the rate-limiting step (RLS) in the initial stage of the Baylis-Hillman reaction, which involves the amine-catalyzed addition of an aldehyde to an activated alkene to generate an allylic alcohol. This finding has considerable implications for asymmetric catalysis of the reaction. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1706 / 1708

页数：3

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