Abstract
This study has demonstrated that the stereochemical outcome of
the direct alkylation of nickel(II) complexes derived from chiral
Schiff bases of glycine, alanine, 2-aminobutyric acid, and leucine
with racemic α-methylbenzyl bromide depends on the steric bulk
of the corresponding amino acid residue. In particular, the alkylation
of the alanine complex was found to proceed with a synthetically
useful level (90% de) of stereoselectivity offering a concise
synthesis of enantiomerically pure (2S ,3S )- or (2R ,3R )-α,β-dimethylphenylalanines.
Key words
sterically constrained amino acids - alkylation - asymmetric
synthesis - kinetic resolution
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