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二烷基锌试剂对开链硝基烯烃的高度对映选择性共轭加成:一种合成β2-氨基酸、醛和醇的催化途径。

Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes: a catalytic route to beta2-amino acids, aldehydes, and alcohols.

作者信息

Duursma Ate, Minnaard Adriaan J, Feringa Ben L

机构信息

Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, The Netherlands.

出版信息

J Am Chem Soc. 2003 Apr 2;125(13):3700-1. doi: 10.1021/ja029817d.

Abstract

Using chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition to acyclic nitroalkenes for the first time, we obtained enantioselectivities up to 98%. The use of acyclic substrates with different dialkylzinc reagents provides a catalytic enantioselective route to (functionalized) beta2-amino aldehydes, acids, and alcohols.

摘要

首次在手性亚磷酰胺配体(S,R,R)-L1对非环状硝基烯烃的共轭加成反应中,我们获得了高达98%的对映选择性。使用带有不同二烷基锌试剂的非环状底物,为制备(官能化的)β2-氨基醛、酸和醇提供了一条催化对映选择性途径。

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