β-tosylethylhydroxylamine: Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations

Gerald D. Artman, Jacob H. Waldman, Steven M. Weinreb

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

An efficient three-step procedure has been developed for synthesis of β-tosylethylhydroxylamine from commercially available starting material. This compound forms hydroxamic acids which undergo amidyl radical-olefin cyclizations promoted by diethyl chlorophosphite to give functionalized β-tosylethyl-protected lactams, which can be deprotected under mild basic conditions.

Original languageEnglish (US)
Pages (from-to)2057-2063
Number of pages7
JournalSynthesis
Issue number14
StatePublished - Oct 29 2002

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Hydroxamic Acids
Lactams
Hydroxylamine
Cyclization
Alkenes
Olefins
Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Artman, Gerald D. ; Waldman, Jacob H. ; Weinreb, Steven M. / β-tosylethylhydroxylamine : Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations. In: Synthesis. 2002 ; No. 14. pp. 2057-2063.
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β-tosylethylhydroxylamine : Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations. / Artman, Gerald D.; Waldman, Jacob H.; Weinreb, Steven M.

In: Synthesis, No. 14, 29.10.2002, p. 2057-2063.

Research output: Contribution to journalArticle

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AU - Waldman, Jacob H.

AU - Weinreb, Steven M.

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