On the interaction of silyl triflates with enamines: iminium ion formation versus silylation

On the interaction of silyl triflates with enamines: iminium ion formation versus silylation Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2005, Volume: 46, Number: 21, Pages: 3729-3732 Pages count : 4 DOI: 10.1016/j.tetlet.2005.03.144

Authors

Levin Vitalij V. ¹ , Dilman Alexander D. ¹ , Belyakov Pavel A. ¹ , Korlyukov Alexander A. ² , Struchkova Marina I. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, 119991 Moscow, Vavilov str. 28, Russian Federation

The interaction of Me3SiOTf and (C6F5)3SiOTf with enamines generating α-silyl-substituted iminium ions is investigated. A trimethylsilyl iminium cation is formed as a long-lived species observable by NMR spectroscopy, whilst the tris(pentafluorophenyl)silyl analogue is very labile and prone to the loss of a proton. On the basis of the latter phenomenon, a method for the synthesis of β-silyl enamines is proposed.

Levin V.V. , Dilman A.D. , Belyakov P.A. , Korlyukov A.A. , Struchkova M.I. , Tartakovsky V.A.
On the interaction of silyl triflates with enamines: iminium ion formation versus silylation
Tetrahedron Letters. 2005. V.46. N21. P.3729-3732. DOI: 10.1016/j.tetlet.2005.03.144 WOS Scopus OpenAlex

Web of science:	WOS:000228872400028
Scopus:	2-s2.0-17944379458
OpenAlex:	W2950551982

DB	Citing
OpenAlex	6
Scopus	5
Web of science	5