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磷化氢催化活化的α,β-不饱和酮与森田-贝利斯-希尔曼碳酸酯的不对称[4+1]环化反应:对映选择性合成含有两个相邻季碳立体中心的螺环氧化吲哚。

Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita-Baylis-Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters.

作者信息

Hu Fang-Le, Wei Yin, Shi Min

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China.

出版信息

Chem Commun (Camb). 2014 Aug 18;50(64):8912-4. doi: 10.1039/c4cc03479a.

Abstract

The asymmetric [4+1] annulation of activated α,β-unsaturated ketones with MBH carbonates catalyzed by bifunctional thiourea-phosphine catalysts derived from an axially chiral binaphthyl scaffold has been developed, giving spirooxindoles with two adjacent quaternary stereocenters in good yields with high enantioselectivities and moderate diastereoselectivities under mild conditions.

摘要

基于轴向手性联萘骨架衍生的双功能硫脲-膦催化剂,实现了活性α,β-不饱和酮与MBH碳酸酯的不对称[4+1]环化反应,在温和条件下以良好的产率、高对映选择性和中等非对映选择性得到了具有两个相邻季碳立体中心的螺环氧化吲哚。

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