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)

Citation
Yn. Belokon' et al., 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), TETRAHEDR L, 42(45), 2001, pp. 8093-8096
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
45
Year of publication
2001
Pages
8093 - 8096
Database
ISI
SICI code
0040-4039(20011105)42:45<8093:TIOISC>2.0.ZU;2-Q
Abstract
Systematic variation of the substrate structure has shown that the most eff ective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chloroph enyl imines of amino esters. The other reaction parameters (solvent and sti rring speed) have also been optimized. The introduction of substituents ont o the aryl rings of the salen ligand was found not to have a beneficial eff ect on the enantioselectivity of the reaction. (C) 2001 Elsevier Science Lt d. All rights reserved.