Palladium-Catalyzed Insertion of α-Diazoesters into Vinyl Halides To Generate α,β-Unsaturated γ-Amino Esters

被引：123

作者：

Kudirka, Romas ^{[1
]}

Devine, Sean K. J. ^{[1
]}

Adams, Christopher S. ^{[1
]}

Van Vranken, David L. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 20期

关键词：

amino acids; C-C coupling; diazo compounds; palladium; peptide mimics; CARBENE INSERTION; DIAZOCARBONYL COMPOUNDS; SECONDARY STRUCTURES; MIGRATORY INSERTION; PEPTIDES; REACTIVITY; ARYL; SUBSTITUTION; NUCLEOPHILES; INHIBITORS;

D O I：

10.1002/anie.200805483

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As easy as 1, 2, 3: A palladium-catalyzed three-component coupling generates α,β - unsaturated γ-amino acids in a single step (see scheme). The reaction is believed to involve migration of a vinyl substituent to a highly electrophilic palladium carbene. Unlike previous synthetic approaches, this synthesis provides access to γ-amino acids with non-natural side chains. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3677 / 3680

页数：4

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[2]

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[3]

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