Journal
TETRAHEDRON
Volume 57, Issue 13, Pages 2491-2498Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00072-2
Keywords
phase-transfer-catalysis; copper; Schiff-bases; asymmetric-catalysis; amino-acid
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Chiral salen-metal complexes have been tested as catalysts for the C-alkylation of Schiffs basis of alanine and glycine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1-10 mol% of the catalyst). The best catalyst, which was derived from a Cu(II) complex of(1R, 2R or 1S,2S)-[N,N'-bis(2'-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave alpha -amino and alpha -methyl-alpha -amino acids with enantiomeric excesses of 70-96%. (C) 2001 Elsevier Science Ltd. All rights reserved.
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