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通过卤化物和一氧化碳催化生成C1铵烯醇盐用于不对称串联反应。

Catalytic Generation of C1 Ammonium Enolates from Halides and CO for Asymmetric Cascade Reactions.

作者信息

Li Lu-Lu, Ding Du, Song Jin, Han Zhi-Yong, Gong Liu-Zhu

机构信息

Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

Collaborative Innovation Center of Chemical Science, and Engineering, Tianjin, China.

出版信息

Angew Chem Int Ed Engl. 2019 Jun 3;58(23):7647-7651. doi: 10.1002/anie.201901501. Epub 2019 May 7.

Abstract

A general strategy for the design of asymmetric cascade reactions using readily available halides and carbon monoxide (CO) as substrates is developed. The key is the catalytic generation of C1-ammonium enolates for the subsequent asymmetric cascade reactions through the combination of palladium-catalyzed carbonylation and chiral Lewis base catalysis. Utilizing this strategy, we have established asymmetric formal [1+1+4] and [1+1+2] reactions to afford chiral dihydropyridones and β-lactams with high yields and high enantio- and diastereoselectivities.

摘要

开发了一种以易于获得的卤化物和一氧化碳(CO)为底物设计不对称串联反应的通用策略。关键在于通过钯催化的羰基化反应和手性路易斯碱催化相结合,催化生成用于后续不对称串联反应的C1-铵烯醇盐。利用这一策略,我们建立了不对称形式的[1+1+4]和[1+1+2]反应,以高产率、高对映选择性和非对映选择性得到手性二氢吡啶酮和β-内酰胺。

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