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Enantioselective Nitroso Aldol Intramolecular Transesterification Cyclization Domino Reaction for Highly Effective Construction of Chiral Spirooxindoles
Author(s) -
Ji ShanPing,
Liu LinWei,
Chen Feng,
Ren HongXia,
Yang Yu,
Zhang ZhengBing,
Peng Lin,
Wang LiXin
Publication year - 2016
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.201600884
Subject(s) - chemistry , enantioselective synthesis , nitrosobenzene , oxindole , bifunctional , aldol reaction , intramolecular force , organic chemistry , transesterification , domino , catalysis , nitroso , cascade reaction , combinatorial chemistry
A catalytic asymmetric nitroso aldol intramolecular transesterification cyclization domino reaction between a C3 alkyl ester substituted oxindole and nitrosobenzene for the construction of chiral spirooxindoles was achieved in the presence of a chiral bifunctional tertiary amine thiourea catalyst and water. Optically active spirooxindoles were obtained in moderate yields (up to 76 %) and excellent enantioselectivities (up to 95 % ee ).