Trimethylsilyl Trifluoromethanesul Fonate (Tmsotf) Catalyzed Amidoalkylation of Silylenolethers. Stereocontrolled Syntheses of (+/-)-Sedamine and (+/-)-Norsedamine
- 1 November 1991
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 21 (21) , 2213-2229
- https://doi.org/10.1080/00397919108055456
Abstract
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl-and N-tert-butoxycarbonyl-2-ethoxypiperidines (3d and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.Keywords
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