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

作者：Biermann Manfred^*; Zheng Guangrong; Hojahmat Marhaba; Moskalev Nick V; Crooks Peter A

来源：Tetrahedron Letters, 2015, 56(20): 2608-2610.

DOI：10.1016/j.tetlet.2015.04.050

• Sharpless asymmetric dihydroxylation
• Ritter reaction
• (S)-Norketamine
• (R)-Norketamine
• Enantioselective synthesis

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.

• 出版日期2015-5-13