The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

Yuri N. Belokon; R. Gareth Davies; José A. Fuentes; Michael North; Teresa Parsons

doi:10.1016/S0040-4039(01)01718-X

The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

Yuri N. Belokon, R. Gareth Davies, José A. Fuentes, Michael North, Teresa Parsons

School of Chemistry

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

33 Citations (Scopus)

Abstract

Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. The other reaction parameters (solvent and stirring speed) have also been optimized. The introduction of substituents onto the aryl rings of the salen ligand was found not to have a beneficial effect on the enantioselectivity of the reaction

Original language	English
Pages (from-to)	8093-8096
Journal	Tetrahedron Letters
Volume	42
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(01)01718-X
Publication status	Published - 5 Nov 2001

Keywords

alpha-amino-acids
practical asymmetric-synthesis
phase transfer catalysis
derivatives

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10.1016/S0040-4039(01)01718-X

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title = "The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)",

abstract = "Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. The other reaction parameters (solvent and stirring speed) have also been optimized. The introduction of substituents onto the aryl rings of the salen ligand was found not to have a beneficial effect on the enantioselectivity of the reaction",

keywords = "alpha-amino-acids, practical asymmetric-synthesis, phase transfer catalysis, derivatives",

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year = "2001",

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The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen). / Belokon, Yuri N.; Davies, R. Gareth; Fuentes, José A. et al.
In: Tetrahedron Letters, Vol. 42, No. 45, 05.11.2001, p. 8093-8096.

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

TY - JOUR

T1 - The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

AU - Belokon, Yuri N.

AU - Davies, R. Gareth

AU - Fuentes, José A.

AU - North, Michael

AU - Parsons, Teresa

PY - 2001/11/5

Y1 - 2001/11/5

N2 - Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. The other reaction parameters (solvent and stirring speed) have also been optimized. The introduction of substituents onto the aryl rings of the salen ligand was found not to have a beneficial effect on the enantioselectivity of the reaction

AB - Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. The other reaction parameters (solvent and stirring speed) have also been optimized. The introduction of substituents onto the aryl rings of the salen ligand was found not to have a beneficial effect on the enantioselectivity of the reaction

KW - alpha-amino-acids

KW - practical asymmetric-synthesis

KW - phase transfer catalysis

KW - derivatives

U2 - 10.1016/S0040-4039(01)01718-X

DO - 10.1016/S0040-4039(01)01718-X

M3 - Article

SN - 0040-4039

VL - 42

SP - 8093

EP - 8096

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

Abstract

Keywords

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