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

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

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

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 language	English (US)
Pages (from-to)	2057-2063
Number of pages	7
Journal	Synthesis
Issue number	14
State	Published - Oct 29 2002

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Cite this

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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.",

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AU - Waldman, Jacob H.

AU - Weinreb, Steven M.

PY - 2002/10/29

Y1 - 2002/10/29

N2 - 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.

AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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