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

19 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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title = "β-tosylethylhydroxylamine: Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations",

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.",

author = "Artman, \{Gerald D.\} and Waldman, \{Jacob H.\} and Weinreb, \{Steven M.\}",

year = "2002",

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language = "English (US)",

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journal = "Synthesis",

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T1 - β-tosylethylhydroxylamine

T2 - Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations

AU - Artman, Gerald D.

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.

UR - https://www.scopus.com/pages/publications/0036398490

UR - https://www.scopus.com/pages/publications/0036398490#tab=citedBy

M3 - Article

AN - SCOPUS:0036398490

SN - 0039-7881

SP - 2057

EP - 2063

JO - Synthesis

JF - Synthesis

IS - 14

ER -

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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