Desulfurization/α-alkylation of β-keto sulfones

Mark J. Kurth, Michael J. O'Brien

Research output: Contribution to journalArticle

45 Scopus citations

Abstract

A one-pot procedure for the reductive alkylation of β-keto sulfones is described. The method proceeds by a lithium in liquid ammonia desulfurization of the starting β-keto sulfone, resulting in regiospecific generation of an intermediate enolate. Subsequent admixture of tributyltin chloride followed by addition of the alkylating agent in HMPA generates the C(α)-alkylated product in good yield and with excellent regiocontrol. Thus, 2-(phenylsulfonyl)-5-(2-propenyl)cyclopentanone gives 2,5-di(2-propenyl)cyclopentanone in 71% isolated yield with <1% of 2,2-di(2-propenyl)cyclopentanone detected in the crude reaction mixture. Experiments are presented which underscore the advantages of this procedure over traditional α-alkylation/desulfurization protocols.

Original languageEnglish (US)
Pages (from-to)3846-3848
Number of pages3
JournalJournal of Organic Chemistry
Volume50
Issue number20
StatePublished - 1985

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Desulfurization/α-alkylation of β-keto sulfones'. Together they form a unique fingerprint.

  • Cite this

    Kurth, M. J., & O'Brien, M. J. (1985). Desulfurization/α-alkylation of β-keto sulfones. Journal of Organic Chemistry, 50(20), 3846-3848.