Asymmetric Synthesis of α,β-Dialkyl-α-phenylalanines via Direct Alkylation of a Chiral Alanine Derivative with Racemic α-Alkylbenzyl Bromides. A Case of High Enantiomer Differentiation at Room Temperature

Vadim A. Soloshonok, Xuejun Tang, Victor J. Hruby, Luc Van Meervelt

Research output: Contribution to journalArticle

84 Scopus citations

Abstract

(Matrix Presented) This study demonstrates that the direct alkylation of a Ni(ll)-complex of the chiral Schiff base of alanine with (S)-o-[N-(N-benzylprolyl)amino]-benzophenone, with racemic α-alkylbenzyl bromides, is a synthetically feasible and methodologically advantageous approach to the target α,β-dialkylphenylalanines over previously reported methods. For the first time we report and rationalize a case of a high enantiomer differentiation process at room temperature.

Original languageEnglish (US)
Pages (from-to)341-343
Number of pages3
JournalOrganic Letters
Volume3
Issue number3
DOIs
StatePublished - Feb 8 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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