Asymmetric synthesis of alpha,beta-dialkyl-alpha-phenylalanines via direct alkylation of a chiral alanine derivative with racemic alpha-alkylbenzyl bromides. A case of high enantiomer differentiation at room temperature.
[figure: see text] This study demonstrates that the direct alkylation of a Ni(II)-complex of the chiral Schiff base of alanine with (S)-o-[N-(N-benzylprolyl)amino]- benzophenone, with racemic alpha-alkylbenzyl bromides, is a synthetically feasible and methodologically advantageous approach to the target alpha,beta-dialkylphenylalanines over previously reported methods. For the first time we report and rationalize a case of a high enantiomer differentiation process at room temperature.
Soloshonok
V A
VA
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Tang
X
X
Hruby
V J
VJ
Van Meervelt
L
L
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000478:Alkylation; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013696:Temperature
D006842:Hydrocarbons, Brominated; D010649:Phenylalanine; D000409:Alanine