Glyoxylates as versatile building blocks for the synthesis of α-amino acid and α-alkoxy acid derivatives via cationic intermediates

被引：32

作者：

Meester, WJN

van Maarseveen, JH

Schoemaker, HE

Hiemstra, H

Rutjes, FPJT

机构：

[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands

[2] DSM Res & Patents, Life Sci Prod, Geleen, Netherlands

[3] Univ Nijmegen, NSRIM, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 14期

关键词：

alpha-alkoxy acids; alpha-amino acids; carbocations; C-C bond formation; glyoxylic acid derivatives;

D O I：

10.1002/ejoc.200200714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glyoxylic acid and its derivatives are versatile ester-substituted aldehyde equivalents that can be used efficiently to generate precursors for reactive cationic intermediates such as iminium ions, N-acyliminium ions, N-sulfonyliminium ions, and oxycarbenium ions. These intermediates have been extensively used for the synthesis of (cyclic) cc-amino acid and alpha-alkoxyester derivatives. The research presented in this review is largely dedicated to the evaluation of the scope and limitations of glyoxylate-derived cationic intermediates in intra- and intermolecular reactions with suitable nucleophiles. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

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页码：2519 / 2529

页数：11

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