Enantiocontrolled Synthesis of β-Branched α-Amino Acids by Using CuI-Catalyzed 1,4-Addition of Glycine Imines to β-Substituted gem-Diactivated Olefins

被引：25

作者：

Hernandez-Toribio, Jorge ^{[1
]}

Gomez Arrayas, Ramon ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, Fac Ciencias, E-28049 Madrid, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 23期

关键词：

amino acids; asymmetric catalysis; conjugate addition; copper; glycinate imines; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; CHIRAL CALCIUM COMPLEXES; DIRECT MANNICH REACTION; AZOMETHINE YLIDES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; MICHAEL REACTION; SCHIFF-BASES; DERIVATIVES; ESTERS;

D O I：

10.1002/chem.201100374

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Branching out! The catalytic asymmetric conjugate addition of glycinate Schiff bases to β-substituted gem-diactivated Michael acceptors under proton transfer conditions gives a variety of β-branched α-amino acids (see scheme; Dpm=diphenylmethylene, EWG=electron-withdrawing group) with excellent levels of diastereo- (typically syn/anti >90:10) and enantiocontrol (90-99 % ee). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6334 / 6337

页数：4

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