Desulfurization of sultams with simultaneous methylenation

Victor O. Rogachev, Sandra Merten, Tobias Seiser, Olga Kataeva, Peter Metz

Research output: Contribution to journal › Article

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

Fingerprint

Keywords

Alkenylation
Alkylation
Desulfurization
Sultams

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Rogachev, V. O., Merten, S., Seiser, T., Kataeva, O., & Metz, P. (2008). Desulfurization of sultams with simultaneous methylenation. Tetrahedron Letters, 49(1), 133-136. https://doi.org/10.1016/j.tetlet.2007.10.153

@article{a49ce1b06e994ce8a57c16241e8ed6bd,

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",

month = "1",

day = "1",

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

language = "English",

volume = "49",

pages = "133--136",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=36549085457&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=36549085457&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2007.10.153

DO - 10.1016/j.tetlet.2007.10.153

M3 - Article

AN - SCOPUS:36549085457

VL - 49

SP - 133

EP - 136

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 1

ER -

Access to Document

10.1016/j.tetlet.2007.10.153