Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom