Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Article abstract of DOI:10.1080/00397919108055456

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.

Full text of DOI:10.1080/00397919108055456

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Synthetic Communications: An
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Trimethylsilyl
Trifluoromethanesul
Fonate (Tmsotf) Catalyzed
Amidoalkylation
of Silylenolethers.
Stereocontrolled Syntheses
of (+/-)-Sedamine and (+/-)-
Norsedamine
R. A. Pilli a & L. C. Dias a
a Universidade Estadual de Campinas, Instituto de
Química , C.P. 615, 13081, Campinas, SP, Brazil
Published online: 18 Nov 2011.
To cite this article: R. A. Pilli & L. C. Dias (1991) Trimethylsilyl Trifluoromethanesul
Fonate (Tmsotf) Catalyzed Amidoalkylation of Silylenolethers. Stereocontrolled
Syntheses of (+/-)-Sedamine and (+/-)-Norsedamine, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry, 21:21,
2213-2229, DOI: 10.1080/00397919108055456
To link to this article: http://dx.doi.org/10.1080/00397919108055456
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