Desulfurization of sultams with simultaneous methylenation

Abstract

Alkylation of γ- and δ-sultams with (iodomethyl)trimethylsilane followed by treatment of the resultant silanes with tetrabutylammonium fluoride gave rise to sulfur-free unsaturated amines. In particular, N-THP substituted sultams were found to be useful substrates for the alkylation event. A corresponding one-pot transformation involving sultam α-alkylation with (iodomethyl)magnesium chloride is also reported.

Original language	English
Pages (from-to)	133-136
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2007.10.153
Publication status	Published - 1 Jan 2008

Keywords

Alkenylation
Alkylation
Desulfurization
Sultams

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.10.153

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title = "Desulfurization of sultams with simultaneous methylenation",

abstract = "Alkylation of γ- and δ-sultams with (iodomethyl)trimethylsilane followed by treatment of the resultant silanes with tetrabutylammonium fluoride gave rise to sulfur-free unsaturated amines. In particular, N-THP substituted sultams were found to be useful substrates for the alkylation event. A corresponding one-pot transformation involving sultam α-alkylation with (iodomethyl)magnesium chloride is also reported.",

keywords = "Alkenylation, Alkylation, Desulfurization, Sultams",

author = "Rogachev, {Victor O.} and Sandra Merten and Tobias Seiser and Olga Kataeva and Peter Metz",

year = "2008",

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doi = "10.1016/j.tetlet.2007.10.153",

language = "English",

volume = "49",

pages = "133--136",

journal = "Tetrahedron Letters",

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T1 - Desulfurization of sultams with simultaneous methylenation

AU - Rogachev, Victor O.

AU - Merten, Sandra

AU - Seiser, Tobias

AU - Kataeva, Olga

AU - Metz, Peter

PY - 2008/1/1

Y1 - 2008/1/1

N2 - Alkylation of γ- and δ-sultams with (iodomethyl)trimethylsilane followed by treatment of the resultant silanes with tetrabutylammonium fluoride gave rise to sulfur-free unsaturated amines. In particular, N-THP substituted sultams were found to be useful substrates for the alkylation event. A corresponding one-pot transformation involving sultam α-alkylation with (iodomethyl)magnesium chloride is also reported.

AB - Alkylation of γ- and δ-sultams with (iodomethyl)trimethylsilane followed by treatment of the resultant silanes with tetrabutylammonium fluoride gave rise to sulfur-free unsaturated amines. In particular, N-THP substituted sultams were found to be useful substrates for the alkylation event. A corresponding one-pot transformation involving sultam α-alkylation with (iodomethyl)magnesium chloride is also reported.

KW - Alkenylation

KW - Alkylation

KW - Desulfurization

KW - Sultams

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DO - 10.1016/j.tetlet.2007.10.153

M3 - Article

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VL - 49

SP - 133

EP - 136

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 1