Synthesis of diastereomerically enriched 2-bromoesters and their reaction with nucleophiles.

2-Bromoesters enriched in the (S,R)-diastereoisomer can be easily prepared by coupling of racemic 2-bromoacids with (R)-pantolactone. Displacement of the bromine atom with nucleophiles, under suitable reaction conditions, occurs without epimerization of starting compounds, giving (R,R)-2-substituted carboxylic acid derivatives. Chirality 13:102–108, 2001. © 2001 Wiley-Liss, Inc.