ENANTIOSELECTIVE REFORMATSKY REACTION INDUCED BY CHIRAL BETA-AMINO ALCOHOLS

Reformatsky reagent derived from tert-butyl alpha-bromoacetate adds to carbonyl compounds in the presence of chiral amino alcohols leading t o beta-hydroxy tert-butyl esters with good e.e. The enantioface differ entiation depends on the reaction conditions and on the structure of t he chiral auxiliary. The best chemical yields and e.e. are obtained fo r aromatic aldehydes by using the C-2 symmetrical chiral bis-amino alc ohol (5) derived from m-xylylene diamine. (C) 1997 Elsevier Science Lt d.