Enantioselective reformatsky reaction induced by chiral β-amino alcohols

Abstract

Reformatsky reagent derived from tert-butyl α-bromoacetate adds to carbonyl compounds in the presence of chiral amino alcohols leading to β-hydroxy tert-butyl esters with good e.e. The enantioface differentiation depends on the reaction conditions and on the structure of the chiral auxiliary. The best chemical yields and e.e. are obtained for aromatic aldehydes by using the C-2 symmetrical chiral bis-amino alcohol ( 5 ) derived from m-xylylene diamine. Reformatsky reagents derived from tert-butyl α-bromoacetate adds to carbonyl compounds in the presence of chiral amino alcohols leading to β-hydroxy tert-butyl esters with good ee.