Ad. Hughes et Ns. Simpkins, SMI2-MEDIATED REDUCTION OF ALPHA-FUNCTIONALIZED AMIDES - HIGHLY ENANTIOSPECIFIC ACCESS TO AN ATROPISOMERIC AMIDE, Synlett, (9), 1998, pp. 967
SmI2 or SmI2-LiCl mixtures can be used to reduce ol-functionalised ami
des in yields of up to 85% depending upon the amide structure. The met
hod has been applied to the synthesis of an atropisomeric anilide syst
em in highly enantioenriched form, starting with (S)-O-acetyl lactic a
cid.