Chiral salen–metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions

Chiral salen–metal complexes have been tested as catalysts for the C-alkylation of Schiff's bases 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 der...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 13; pp. 2491 - 2498
Main Authors Belokon, Yuri N, North, Michael, Churkina, Tatiana D, Ikonnikov, Nikolai S, Maleev, Victor I
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.03.2001
Elsevier
Subjects
amino-acid
asymmetric-catalysis
Chemistry
Chemistry, Organic
copper
phase-transfer-catalysis
Physical Sciences
Schiff-bases
Science & Technology
copper
asymmetric-catalysis
phase-transfer-catalysis
amino-acid
Schiff-bases
QUATERNARY AMMONIUM SALT
ENANTIOSELECTIVE SYNTHESIS
ALKYLATION
ESTERS
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Summary:Chiral salen–metal complexes have been tested as catalysts for the C-alkylation of Schiff's bases 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 (1 R, 2 R or 1 S,2 S)-[ N, N′-bis(2′-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave α-amino and α-methyl-α-amino acids with enantiomeric excesses of 70–96%. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00072-2