ChemInform Abstract: Enantioselective Synthesis of α‐Bromo Acid Derivatives and Bromohydrins from Tartrate Derived Bromoacetals.

Abstract

2000 stereochemistry stereochemistry (general, optical resolution) O 0030 -029Enantioselective Synthesis of α-Bromo Acid Derivatives and Bromohydrins from Tartrate Derived Bromoacetals.-Bromination of optically active acetals (I) give in most cases products which can be recrystallized to stereochemical purity. α-Bromoketones (IIIc)-(IIIe), derived from the corresponding bromoacetals by hydrolysis, undergo Baeyer-Villiger oxidation to afford α-bromoesters (IV) with minimal racemization as is assessed by conversion to esters (VI) or amides (VIII). Ketone (IIc) is reduced to bromohydrin (IX) with retention of stereochemistry. -(BOYES, SCOTT A.; HEWSON, ALAN T.; Perkin 1 (2000) 16, 2759-2765; Div. Chem., Sheffield Hallam Univ., Sheffield S1 1WB, UK; EN)