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

Author:
Biermann, Manfred, Zheng, Guangrong, Hojahmat, Marhaba, Moskalev, Nick V., Crooks, Peter A.
Source:
Tetrahedron letters 2015 v.56 no.20 pp. 2608-2610
ISSN:
0040-4039
Subject:
X-radiation, amination, dihydroxylation, enantiomers, organic compounds, oxidation
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.
Agid:
6025406