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DOI10.1038/ncomms14510
Catalytic enantioselective addition of organometallics to unprotected carboxylic acids
Yan, Xingchen; Harutyunyan, Syuzanna R.
2019-07-30
发表期刊NATURE COMMUNICATIONS
ISSN2041-1723
出版年2019
卷号10
文章类型Article
语种英语
国家Netherlands
英文摘要

Conjugate addition of organometallics to carbonyl based Michael acceptors is a widely used method that allows the building of new carbon-carbon (C-C) bonds and the introduction of chirality in a single step. However, conjugate additions to the simplest Michael acceptors, namely unprotected, unsaturated carboxylic acids, are considered to be prohibited by the fact that acid-base reactions overpower any other type of reactivity, including nucleophilic addition. Here we describe a transient protecting group strategy that allows efficient catalytic asymmetric additions of organomagnesium reagents to unprotected alpha,beta-unsaturated carboxylic acids. This unorthodox pathway is achieved by preventing the formation of unreactive carboxylate salts by means of a reactive intermediate, allowing modifications of the carbon chain to proceed unhindered, while the stereochemistry is controlled with a chiral copper catalyst. A wide variety of beta-chiral carboxylic acids, obtained with excellent enantioselectivities and yields, can be further transformed into valuable molecules through for instance catalytic decarboxylative cross-coupling reactions.


领域资源环境
收录类别SCI-E
WOS记录号WOS:000477860700008
WOS关键词ASYMMETRIC CONJUGATE ADDITION ; GRIGNARD-REAGENTS ; ARYLBORONIC ACIDS ; ALKYLATION ; ESTERS ; LIGHT
WOS类目Multidisciplinary Sciences
WOS研究方向Science & Technology - Other Topics
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文献类型期刊论文
条目标识符http://119.78.100.173/C666/handle/2XK7JSWQ/203222
专题资源环境科学
作者单位Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands
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Yan, Xingchen,Harutyunyan, Syuzanna R.. Catalytic enantioselective addition of organometallics to unprotected carboxylic acids[J]. NATURE COMMUNICATIONS,2019,10.
APA Yan, Xingchen,&Harutyunyan, Syuzanna R..(2019).Catalytic enantioselective addition of organometallics to unprotected carboxylic acids.NATURE COMMUNICATIONS,10.
MLA Yan, Xingchen,et al."Catalytic enantioselective addition of organometallics to unprotected carboxylic acids".NATURE COMMUNICATIONS 10(2019).
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