Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations

Chiral, salen-metal complexes have been tested as catalysts for the C-alkylation of aldimine Schiff's bases of alanine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1–10% of the catalyst). The best catalyst, which was derived f...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 33; pp. 6105 - 6108
Main Authors Belokon, Yuri N., North, Michael, Kublitski, Vadim S., Ikonnikov, Nikolai S., Krasik, Pavel E., Maleev, Viktor I.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.08.1999
Elsevier
Subjects
amino acid
asymmetric synthesis
catalysis
Chemistry
Chemistry, Organic
copper
Phase transfer
Physical Sciences
Science & Technology
catalysis
copper
asymmetric synthesis
Phase transfer
amino acid
CINCHONA ALKALOIDS
ENANTIOSELECTIVE SYNTHESIS
ALPHA-AMINO-ACIDS
DERIVATIVES
EPOXIDATION
phase transfer
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Summary:Chiral, salen-metal complexes have been tested as catalysts for the C-alkylation of aldimine Schiff's bases of alanine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1–10% 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-methyl-α-amino acids with enantiomeric excesses of 70–96%. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01214-9