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手性铜配合物催化2-取代苯并呋喃-3(2H)-酮与α,β-不饱和酮的不对称共轭加成反应。

Asymmetric conjugate additions of 2-substituted benzofuran-3(2H)-ones to α,β-unsaturated ketones catalyzed by chiral copper complexes.

作者信息

Wang Haojiang, Wang Yifeng, Zhang Cheng, Jiang Yidong, Chu Mingming, Li Zhaobo, Du Xiaohua, Xu Danqian

机构信息

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

出版信息

Org Biomol Chem. 2017 May 16;15(19):4191-4198. doi: 10.1039/c7ob00677b.

Abstract

A highly enantioselective conjugate addition of 2-substituted benzofuran-3(2H)-ones to α,β-unsaturated ketones promoted by chiral copper complexes has been developed, affording the Michael addition products with quaternary stereocenters in good to high yields (up to 95% yield) with excellent enantioselectivities (up to 99% ee). The chiral Michael adducts could be readily converted to the polycyclic benzofuran-type framework via the Robinson annulation.

摘要

已经开发了一种在手性铜配合物促进下,2-取代苯并呋喃-3(2H)-酮与α,β-不饱和酮的高度对映选择性共轭加成反应,以良好至高产率(高达95%产率)和优异对映选择性(高达99% ee)得到具有季碳立体中心的迈克尔加成产物。手性迈克尔加合物可通过罗宾逊缩环反应轻松转化为多环苯并呋喃型骨架。

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