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通过钴催化的不对称逆异戊烯基化反应构建连位季碳中心

Construction of Vicinal Quaternary Carbon Centers via Cobalt-Catalyzed Asymmetric Reverse Prenylation.

作者信息

Sun Minghe, Chen Jia-Feng, Chen Shufeng, Li Changkun

机构信息

Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering , Inner Mongolia University , Hohhot 010021 , People's Republic of China.

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , People's Republic of China.

出版信息

Org Lett. 2019 Mar 1;21(5):1278-1282. doi: 10.1021/acs.orglett.8b04030. Epub 2019 Feb 15.

Abstract

A highly enantioselective cobalt-catalyzed reverse prenylation of β-ketoester with tertiary allylic carbonate to construct vicinal all-carbon quaternary carbon centers has been developed. By using the cobalt/( S, S)Ph-BPE complex generated in situ with zinc reduction, excellent branched to linear selectivity (>20:1) and up to 92% ee have been obtained.

摘要

已开发出一种通过钴催化β-酮酯与叔烯丙基碳酸酯进行高度对映选择性的反向异戊烯基化反应来构建相邻全碳季碳中心的方法。通过使用原位生成的钴/(S,S)-Ph-BPE配合物并进行锌还原,可获得出色的支链与线性选择性(>20:1)以及高达92%的对映体过量(ee)。

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