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Asymmetric Formal [3+2] Cycloaddition Reaction of α‐Aryl Isocyanoesters with N ‐Aryl Maleimides by Bifunctional Cinchona Alkaloids‐Based Squaramide/AgSbF 6 Cooperative Catalysis
Author(s) -
Zhao MeiXin,
Wei DengKe,
Ji FeiHu,
Zhao XiaoLi,
Shi Min
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200686
Subject(s) - squaramide , enantioselective synthesis , bifunctional , cinchona , cycloaddition , aryl , chemistry , maleimide , catalysis , organocatalysis , pyrrole , combinatorial chemistry , organic chemistry , medicinal chemistry , alkyl
It is better to be cooperative : A highly diastereo‐ and enantioselective asymmetric [3+2] cycloaddition reaction of α‐aryl isocyanoacetates with N ‐aryl maleimides through cooperative catalysis of cinchona alkaloid‐derived squaramide/AgSbF 6 was developed. A wide range of optically active, substituted 1,3a,4,5,6,6a‐hexahydropyrrolo[3,4‐c] pyrrole derivatives was obtained in high yields (up to 98 %), high diastereoselectivities (>20:1 d.r.), and good to excellent enantioselectivities (up to 92 % ee ) under mild reaction conditions.