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Synlett 2010(4): 628-632
DOI: 10.1055/s-0029-1219365
DOI: 10.1055/s-0029-1219365
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkNew Regiospecific Catalytic Approaches to 4,5-Dihydroisoxazoles and 2,5-Dihydroisoxazoles from O-Propargylic Hydroxylamines
Further Information
Received
9 November 2009
Publication Date:
02 February 2010 (online)
Publication History
Publication Date:
02 February 2010 (online)
Abstract
Unprotected O-propargylic hydroxylamines undergo generally essentially quantitative cyclisations when exposed briefly to silver nitrate adsorbed onto silica gel to give 4,5-dihydroisoxazoles [2-isoxazolines], while N-protected derivatives give the corresponding 2,5-dihydroisoxazoles [3-isoxazolines] in similarly excellent yields, given that an appropriate functionality on nitrogen is used.
Key words
4,5- and 2,5-dihydroisoxazoles - O-propargylic hydroxylamines - cyclisations - silver nitrate on silica gel
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References
Hatherley J. L., Knight D. W. unpublished observations.