Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction

被引：64

作者：

Steurer, Marianne ^{[1
]}

Jensen, Kim L. ^{[1
]}

Worgull, Dennis ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 01期

基金：

奥地利科学基金会;

关键词：

amino esters; asymmetric synthesis; cycloaddition; organocatalysis; phosphines; MORITA-BAYLIS-HILLMAN; ELECTRON-DEFICIENT OLEFINS; PROMOTED 3+2 ANNULATIONS; FUNCTIONALIZED CYCLOPENTENES; ASYMMETRIC-SYNTHESIS; CYCLOADDITIONS; ALLENES; ACID; 2,3-BUTADIENOATES; ORGANOCATALYSTS;

D O I：

10.1002/chem.201103502

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phosphines go one-pot: The one-pot synthesis of cyclic α-amino esters from azlactones and allenes by a phosphine-catalyzed [3+2]-cycloaddition reaction followed by a ring opening of the azlactone moiety is presented. The products are isolated as single regioisomers in good overall yields and high enantioselectivities (up to 95% ee). The possibility for easy modifications of the obtained products was demonstrated by synthesizing an amino acid and an α-hydroxy-β-ketoester. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：76 / 79

页数：4

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