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DOI | 10.1038/ncomms14510 |
Catalytic enantioselective addition of organometallics to unprotected carboxylic acids | |
Yan, Xingchen; Harutyunyan, Syuzanna R. | |
2019-07-30 | |
发表期刊 | NATURE COMMUNICATIONS
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ISSN | 2041-1723 |
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 |
URL | 查看原文 |
引用统计 | |
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 |
推荐引用方式 GB/T 7714 | 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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