Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides

被引：6

作者：

Wang, Jie ^{[1
]}

Li, Xin ^{[1
]}

Cheng, Jin-Pei ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn, Coll Chem, Tianjin 300071, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2019年 / 62卷 / 05期

基金：

中国国家自然科学基金;

关键词：

michael addition; 3,3 '-disubstituted phthalides; vicinal quaternary-tertiary stereogenic centers; ASYMMETRIC CONJUGATE ADDITION; CARBOXYLIC-ACIDS; FACILE ACCESS; QUATERNARY; DIHYDRONAPHTHOQUINONES; BENZOFURAN-2(3H)-ONES; BENZOFURAN-2-ONES; STEREOCENTERS; DERIVATIVES; CYCLIZATION;

D O I：

10.1007/s11426-018-9393-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereoselective and enantioselective Michael addition/desymmetrization reaction of maleimides with prochiral 3- substituted phthalides catalyzed by quinine-derived bifunctional thiourea was realized. A broad range of the 3,3-disubstituted phthalides bearing vicinal quaternary-tertiary stereogenic centers were synthesized in moderate to good yields (up to 96%) with high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 96:4 er).

引用

页码：649 / 652

页数：4

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