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Bicyclic‐Guanidine‐Catalyzed Asymmetric Michael Addition of 3‐Substituted Oxindoles to 2‐Cyclopentenone
Author(s) -
Yang Caiyun,
Chen Wenchao,
Yang Wenguo,
Zhu Bo,
Yan Lin,
Tan ChoonHong,
Jiang Zhiyong
Publication year - 2013
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.201301011
Subject(s) - michael reaction , adduct , guanidine , cyclopentenone , variety (cybernetics) , yield (engineering) , computer science , chemistry , catalysis , organic chemistry , artificial intelligence , physics , thermodynamics
Taking the Michael : The first highly enantio‐ and diastereoselective Michael addition of various 3‐benzyl‐substituted oxindoles to 2‐cyclopentenone has been developed. A variety of 3,3‐disubstituted oxindoles as Michael adducts were obtained in 69–99 % yield with 73–98 % ee and 9:1 to >20:1 d.r.