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对映选择性质子化。

Enantioselective protonation.

机构信息

Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Mail Code 164-30, Pasadena, CA 91125, USA.

出版信息

Nat Chem. 2009 Aug;1(5):359-69. doi: 10.1038/nchem.297.

DOI:10.1038/nchem.297
PMID:20428461
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2860147/
Abstract

Enantioselective protonation is a common process in biosynthetic sequences. The decarboxylase and esterase enzymes that effect this valuable transformation are able to control both the steric environment around the proton acceptor (typically an enolate) and the proton donor (typically a thiol). Recently, several chemical methods to achieve enantioselective protonation have been developed by exploiting various means of enantiocontrol in different mechanisms. These laboratory transformations have proven useful for the preparation of a number of valuable organic compounds.

摘要

对映选择性质子化是生物合成序列中的常见过程。实现这一有价值转化的脱羧酶和酯酶能够控制质子受体(通常为烯醇化物)和质子供体(通常为硫醇)周围的立体环境。最近,通过利用不同机制中的各种对映体控制手段,已经开发出了几种实现对映选择性质子化的化学方法。这些实验室转化对于制备许多有价值的有机化合物非常有用。

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本文引用的文献

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Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation.不对称合成和立体选择性反应中的非线性效应:十年研究
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Enantioselective enolate protonations: Friedel-Crafts reactions with alpha-substituted acrylates.对映选择性烯醇盐质子化反应:与α-取代丙烯酸酯的傅-克反应
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