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
收藏
页码：649 / 652
页数：4
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