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Direct Asymmetric anti ‐Mannich‐Type Reactions Catalyzed by Cinchona Alkaloid Derivatives
Author(s) -
Jin Ying,
Chen Di,
Zhang Xiu Rong
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22358
Subject(s) - chemistry , cinchona , aldimine , oxindole , alkaloid , mannich reaction , organic chemistry , catalysis , enantioselective synthesis , cinchona alkaloids , organocatalysis , stereochemistry
A series of cinchona alkaloid derivatives were used to catalyze the asymmetric anti ‐Mannich‐type reaction of 3‐methyl‐2‐oxindole with N ‐tosyl aryl aldimines. The resulting anti ‐3,3‐disubstituted 2‐oxindole products were obtained in good yields (up to 92%) with high diastereo‐ and enantioselectivities ( anti/syn up to 97:3 and 91% ee). Chirality 26:801–805, 2014 . © 2014 Wiley Periodicals, Inc.