Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues

Article abstract of DOI:10.1016/0957-4166(96)00122-X

From a single chiron (R)-(+)-5, available with high enantiomeric excess (97%) by enzymatic hydrolysis (PLE acetonic powder) of a malonate, were prepared convenient precursors of aminoglutethimides (-)-AG-1 and (+)-AG-1. This versatile method also allows preparation of the b-hydroxy ester (R)-9 and its enantiomer (S)-9 as well as the glutethimides (S)-4 and (R)-4 and other analogues.