立体选择性
对映选择合成
化学
催化作用
对映体
背景(考古学)
有机化学
组合化学
酶催化
对映体过量
生物
古生物学
作者
Hui Zhou,Yu Zhou,Han Yong Bae,Markus Leutzsch,Yihang Li,Chandra Kanta De,Gui‐Juan Cheng,Benjamin List
出处
期刊:Nature
[Springer Nature]
日期:2022-05-04
卷期号:605 (7908): 84-89
被引量:39
标识
DOI:10.1038/s41586-022-04531-5
摘要
Enzymatic stereoselectivity has typically been unrivalled by most chemical catalysts, especially in the conversion of small substrates. According to the 'lock-and-key theory'1,2, enzymes have confined active sites to accommodate their specific reacting substrates, a feature that is typically absent from chemical catalysts. An interesting case in this context is the formation of cyanohydrins from ketones and HCN, as this reaction can be catalysed by various classes of catalysts, including biological, inorganic and organic ones3-7. We now report the development of broadly applicable confined organocatalysts for the highly enantioselective cyanosilylation of aromatic and aliphatic ketones, including the challenging 2-butanone. The selectivity (98:2 enantiomeric ratio (e.r.)) obtained towards its pharmaceutically relevant product is unmatched by any other catalyst class, including engineered biocatalysts. Our results indicate that confined chemical catalysts can be designed that are as selective as enzymes in converting small, unbiased substrates, while still providing a broad scope.
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