Synthesis of alpha-amino esters by dynamic kinetic resolution of alpha-haloacyl imidazolidinones

Authors
Caddick, S Afonso, CAM Candeias, SX Hitchcock, PB Jenkins, K Murtagh, L Pardoe, D Santos, AG Treweeke, NR Weaving, R
Citation
S. Caddick et al., Synthesis of alpha-amino esters by dynamic kinetic resolution of alpha-haloacyl imidazolidinones, TETRAHEDRON, 57(30), 2001, pp. 6589-6605
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
30
Year of publication
2001
Pages
6589 - 6605
Database
ISI
SICI code
0040-4020(20010723)57:30<6589:SOAEBD>2.0.ZU;2-H
Abstract
Dynamic kinetic resolution of alpha -haloacyl imidazolidinones with a varie ty of nitrogen and carbon nucleophiles has been achieved with selectivities up to 100% (d.e.). An unusual dichotomy of diastereoselection has been obs erved whereby metalated nucleophiles preferentially react via the 5S,2 'R d iastereomer whilst amine nucleophiles react via the 5S,2 'S diastereomer. M ild procedures are described for the coupling and removal of the ephedrine based chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.