Desulfurization of sultams with simultaneous methylenation

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

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    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 languageEnglish
    Pages (from-to)133-136
    Number of pages4
    JournalTetrahedron Letters
    Volume49
    Issue number1
    DOIs
    Publication statusPublished - 1 Jan 2008

    Fingerprint

    Alkylation
    Desulfurization
    Silanes
    Magnesium Chloride
    Sulfur
    Amines
    Substrates
    naphthosultone

    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

    Desulfurization of sultams with simultaneous methylenation. / Rogachev, Victor O.; Merten, Sandra; Seiser, Tobias; Kataeva, Olga; Metz, Peter.

    In: Tetrahedron Letters, Vol. 49, No. 1, 01.01.2008, p. 133-136.

    Research output: Contribution to journalArticle

    Rogachev, VO, Merten, S, Seiser, T, Kataeva, O & Metz, P 2008, 'Desulfurization of sultams with simultaneous methylenation', Tetrahedron Letters, vol. 49, no. 1, pp. 133-136. https://doi.org/10.1016/j.tetlet.2007.10.153
    Rogachev VO, Merten S, Seiser T, Kataeva O, Metz P. Desulfurization of sultams with simultaneous methylenation. Tetrahedron Letters. 2008 Jan 1;49(1):133-136. https://doi.org/10.1016/j.tetlet.2007.10.153
    Rogachev, Victor O. ; Merten, Sandra ; Seiser, Tobias ; Kataeva, Olga ; Metz, Peter. / Desulfurization of sultams with simultaneous methylenation. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 1. pp. 133-136.
    @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 -