Asymmetric synthesis of (S)- and (R)-norketamine via Sharpless asymmetric dihydroxylation/Ritter amination sequence

Abstract Asymmetric synthesis of ( S )-norketamine and ( R )-norketamine utilizing Sharpless asymmetric dihydroxylation followed by stereo-controlled Ritter amination and Jones oxidation is reported. This method allowed the preparation of the free base of ( S )-norketamine and ( R )-norketamine in pure crystalline form for the first time. The absolute configuration of both enantiomers was verified by X-ray structure and optical resolution of racemic norketamine.