Premium
Enantioselective [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Trifluoromethylated 2‐Butenedioic Acid Diesters
Author(s) -
Du Dan,
Jiang Yu,
Xu Qin,
Tang XiangYing,
Shi Min
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500141
Subject(s) - stereocenter , enantioselective synthesis , chemistry , trifluoromethyl , quaternary carbon , organocatalysis , catalysis , combinatorial chemistry , organic chemistry , stereochemistry , alkyl
The highly efficient organocatalytic enantioselective [3+2] cyclization of 3‐isothiocyanato oxindoles with trifluoromethylated 2‐butenedioic acid diesters for the synthesis of spirooxindoles possessing a CF 3 ‐containing quaternary carbon stereocenter was explored. An enantiodivergent approach for the synthesis of spirooxindoles by regulation of the temperature was demonstrated at different temperatures. The outcome of the reaction featured high diastereo‐ and enantioselectivities. Several interesting enantioenriched spirooxindole derivatives bearing a trifluoromethyl quaternary carbon stereocenter were synthesized from the products of this reaction.