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

82 Citations (Scopus)

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

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phenylalanine
Enantiomers
Schiff Bases
enantiomers
alkylation
Alkylation
alanine
Phenylalanine
Bromides
Alanine
imines
bromides
Derivatives
Temperature
room temperature
synthesis
matrices
benzophenone

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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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.",
author = "Soloshonok, {Vadim A.} and Xuejun Tang and Hruby, {Victor J} and {Van Meervelt}, Luc",
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T1 - 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

AU - Soloshonok, Vadim A.

AU - Tang, Xuejun

AU - Hruby, Victor J

AU - Van Meervelt, Luc

PY - 2001/2/8

Y1 - 2001/2/8

N2 - (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.

AB - (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.

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