S. Caddick et al., Synthesis of alpha-amino esters by dynamic kinetic resolution of alpha-haloacyl imidazolidinones, TETRAHEDRON, 57(30), 2001, pp. 6589-6605
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.