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Asymmetric Conjugate Addition to Cyclic Enone Catalyzed by Cu-NHC Complexes with C2 Symmetry

✍ Scribed by Fengjun Shan; Lan Jiang; Zhengning Li; Defeng Zhao

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 108 KB
Volume: 29
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.201190198

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✦ Synopsis

Abstract

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.

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