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Glyoxylates as Versatile Building Blocks for the Synthesis of α‐Amino Acid and α‐Alkoxy Acid Derivatives via Cationic Intermediates
Author(s) -
Meester Wim J. N.,
Maarseveen Jan H. van,
Schoemaker Hans E.,
Hiemstra Henk,
Rutjes Floris P. J. T.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200714
Subject(s) - chemistry , iminium , cationic polymerization , glyoxylic acid , nucleophile , reactive intermediate , alkoxy group , combinatorial chemistry , organic chemistry , aldehyde , ion , catalysis , alkyl
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) α‐amino acid and α‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)