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Highly Enantioselective Organocatalytic Michael Addition/Cyclization Cascade Reaction of Ylideneoxindoles with Isothiocyanato Oxindoles: A Formal [3+2] Cycloaddition Approach to Optically Active Bispirooxindole Derivatives
Author(s) -
Tan Fen,
Cheng HongGang,
Feng Bin,
Zou YouQuan,
Duan ShuWen,
Chen JiaRong,
Xiao WenJing
Publication year - 2013
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.201300081
Subject(s) - stereocenter , enantioselective synthesis , cycloaddition , chemistry , michael reaction , organocatalysis , optically active , cascade reaction , combinatorial chemistry , formal synthesis , stereochemistry , cascade , organic chemistry , catalysis , chromatography
A formal [3+2] cycloaddition involving the organocatalytic asymmetric Michael addition/cyclization cascade reaction of ylideneoxindoles with isothiocyanato oxindoles was developed. This method allows efficient and rapid synthesis of highly functionalized bispirooxindole products bearing three contiguous stereogenic centers with two quaternary stereocenters in almost quantitative yields with extremely high enantio‐ and diastereoselectivities.