ChemInform Abstract: Asymmetric Reactions Catalyzed by Chiral Metal Complexes. Part 27. Efficient Asymmetric Hydrogenation of α‐Aminoacetophenone Derivatives Leading to Practical Synthesis of (S)‐(‐)‐Levamisole.

Abstract

ChemInform Abstract The diphosphines (I) are employed as ligands in the asymmetric hydrogenation of the α-amino ketones (II) to give selectively the (S)-configurated amino alcohols (III). (IIIb) reacts with potassium thiocyanate (IV), producing the optically active iminothiazolidine (V) which is a precursor of (S)-levamisole (VI).

Asymmetric Hydrogenation of Prochiral Amino Ketones to Amino Alcohols for Pharmaceutical Use

“…A secondary R-amino ketone substituted with a chloroethyl group at the nitrogen, a precursor for the immunoregulating drug levamisole, has been asymmetrically hydrogenated using the Rh-MCCPM system, yielding an impressive ee value and TON (Scheme 13) 48 .…”