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

doi:10.1021/ol000330o

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 journal › Article › peer-review

93 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 language	English (US)
Pages (from-to)	341-343
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	3
DOIs	https://doi.org/10.1021/ol000330o
State	Published - Feb 8 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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. / Soloshonok, Vadim A.; Tang, Xuejun; Hruby, Victor J. et al.
In: Organic Letters, Vol. 3, No. 3, 08.02.2001, p. 341-343.

Research output: Contribution to journal › Article › peer-review

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AU - Van Meervelt, Luc

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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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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

Abstract

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