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Asymmetric Conjugate Addition to Cyclic Enone Catalyzed by Cu‐NHC Complexes with C 2 Symmetry
Author(s) -
Shan Fengjun,
Jiang Lan,
Li Zhengning,
Zhao Defeng
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201190198
Subject(s) - chemistry , enone , diethylzinc , conjugate , enantiomer , catalysis , addition reaction , alkoxy group , carbene , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , mathematics , alkyl
A series of chiral, C 2 symmetric tridentate N ‐heterocyclic carbene precursors, containing two N ‐functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex‐2‐enone and cyclopent‐2‐enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee , and 65% ee , respectively. Flip of major enantiomer was observed when different bases or copper sources were utilized.