A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

Jetty L. Duffy, Mark J. Kurth

Research output: Contribution to journal › Article

14 Citations (Scopus)

Abstract

The novel transformation (1 → 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.

Original languageEnglish (US)
Pages (from-to)3783-3785
Number of pages3
JournalJournal of Organic Chemistry
Volume59
Issue number14
StatePublished - 1994

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Cycloaddition
Acids
Alkenes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes. / Duffy, Jetty L.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 59, No. 14, 1994, p. 3783-3785.

Research output: Contribution to journal › Article

Duffy, JL & Kurth, MJ 1994, 'A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes', Journal of Organic Chemistry, vol. 59, no. 14, pp. 3783-3785.
Duffy JL, Kurth MJ. A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes. Journal of Organic Chemistry. 1994;59(14):3783-3785.
Duffy, Jetty L. ; Kurth, Mark J. / A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes. In: Journal of Organic Chemistry. 1994 ; Vol. 59, No. 14. pp. 3783-3785.
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