Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes
Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes
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DOI：
10.1021/acs.joc.7b00571
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发表时间：
2017-05-05
影响因子：
3.6
通讯作者：
Zou, Gang
中科院分区：
文献类型：
--
作者：
Jin, Qaowen;Zheng, Changwu;Zou, Gang
报道了一种在手性双功能季铵盐催化下3-取代羟吲哚与β-卤代烯烃酮/酯的高Z-选择性不对称共轭加成反应。该反应提供了在温和条件下以高产率（高达90%）和良好至高的立体选择性（高达>19：1的Z/E和91%ee）有效地获得一系列具有手性不稳定的Z-烯烃结构和手性季碳中心的2-氧代吲哚衍生物的途径。
A highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to beta-haloalkene ketones/esters catalyzed by readily available chiral bifunctional quaternary ammonium salts is reported. This reaction provides efficient access to a range of 2-oxoindole derivatives bearing a thermodynamically unstable Z-olefin structure and a chiral quaternary carbon center in high yields (up to 90%) and with good to high stereoselectivities (up to >19:1 Z/E and 91% ee) under mild conditions.