Chiral Bifunctional N-Heterocyclic
Carbenes: Synthesis and Application in the Aza-Morita-Baylis-Hillman
Reaction

Lin He; Yan-Rong Zhang; Xue-Liang Huang; Song Ye

doi:10.1055/s-2008-1067216

SPECIALTOPIC

Chiral Bifunctional N-Heterocyclic Carbenes: Synthesis and Application in the Aza-Morita-Baylis-Hillman Reaction

Lin He, Yan-Rong Zhang, Xue-Liang Huang, Song Ye*
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. of China
Fax: +86(10)62654449; e-Mail: songye@iccas.ac.cn;

Abstract

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Abstract

A series of chiral bifunctional N-heterocyclic carbene (NHC) precursors with a proximal hydroxy group were smoothly prepared from l-pyroglutamic acid. Promising enantiomeric excesses (up to 44% ee) were achieved for the bifunctional NHC-catalyzed enantioselective aza-Morita-Baylis-Hillman reaction of cyclopent-2-enone with N-tosylphenylmethanimine.

Key words

N-heterocyclic carbenes - bifunctional catalysts - enantioselective synthesis - aza-Morita-Baylis-Hillman reaction

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Referenzen

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