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Metal‐Free Asymmetric 1,3‐Dipolar Cycloaddition of N ‐Arylmaleimides to Azomethine Ylides Catalyzed by Chiral Tertiary Amine Thiourea
Author(s) -
Bai JianFei,
Wang LiangLiang,
Peng Lin,
Guo YunLong,
Ming JunNan,
Wang FeiYing,
Xu XiaoYing,
Wang LiXin
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100205
Subject(s) - chemistry , thiourea , pyrrolidine , cycloaddition , 1,3 dipolar cycloaddition , catalysis , amine gas treating , enantioselective synthesis , tertiary amine , organic chemistry , polymer chemistry , combinatorial chemistry
The first metal‐free asymmetric 1,3‐dipolar cycloaddition of N ‐arylmaleimides to azomethine ylides catalyzed by chiral tertiary amine thiourea to form multiply substituted pyrrolidines in excellent yields (up to 89 %) and enantioselectivities (up to 96 % ee ) is presented. This procedure allows a rapid diversity‐oriented synthesis of chiral pyrrolidine derivatives with high optical purity.