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Highly Enantioselective Michael Addition of 3‐Aryloxindoles to Phenyl Vinyl Sulfone Catalyzed by Cinchona Alkaloid‐Derived Bifunctional Amine–Thiourea Catalysts Bearing Sulfonamide as Multiple Hydrogen‐Bonding Donors
Author(s) -
Zhao MeiXin,
Tang WenHao,
Chen MingXiao,
Wei DengKe,
Dai TongLei,
Shi Min
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.201100791
Subject(s) - enantioselective synthesis , chemistry , bifunctional , cinchona , sulfonamide , thiourea , michael reaction , catalysis , organic chemistry , organocatalysis , sulfone , amine gas treating
A highly enantioselective Michael addition of 3‐aryloxindole to phenyl vinyl sulfone catalyzed by a quinine‐derived bifunctional amine–thiourea‐bearing sulfonamide as multiple hydrogen‐bonding donor catalyst has been investigated. The corresponding adducts, which contain a chiral quaternary carbon center at the 3‐position of the oxindole, were obtained in moderate‐to‐good yields (52–86 %) with high‐to‐excellent enantioselectivities (83–98 % ee ).
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