Enantioselective Organocatalytic Addition of Oxazolones to 1,1-Bis(phenylsulfonyl)ethylene: A Convenient Asymmetric Synthesis of Quaternary α-Amino Acids

被引：95

作者：

Alba, Andrea-Nekane R. ^{[1
]}

Companyo, Xavier ^{[1
]}

Valero, Guillem ^{[1
]}

Moyano, Albert ^{[1
]}

Rios, Ramon ^{[1
]}

机构：

[1] Univ Barcelona, Dept Organ Chem, Fac Chem, E-08028 Barcelona, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 18期

关键词：

amino acids; Michael addition; organocatalysis; oxazolones; stereoselectivity; PHASE-TRANSFER CATALYSTS; MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; MEMORY; ALKYLATION; CHIRALITY; CONSTRUCTION; STEREOCENTERS; DERIVATIVES;

D O I：

10.1002/chem.200903025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, easy, and highly enantioselective method for the synthesis of quaternary alpha-alkyl-alpha-amino acids based on organocatalysis is reported. The addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene is efficiently catalyzed by simple chiral bases or thioureas. The reaction affords alpha,alpha-disubstituted alpha-amino acid derivatives with complete C4 regioselectivity and with excellent yields and enantioselectivities. This methodology is complementary to previously reported enantioselective approaches to quaternary alpha-amino acids and allows the synthesis of alpha-phenyl-alpha-alkyl-alpha-amino acids and alpha-tert-butyl-alpha-alkyl-alpha-amino acids. It has distinct advantages in terms of operational simplicity, enviromentally friendly conditions, and suitability for largescale reactions.

引用

页码：5354 / 5361

页数：8

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