A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes

Jetty L. Duffy, Mark J. Kurth

Research output: Contribution to journalArticle

14 Scopus citations

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

ASJC Scopus subject areas

  • Organic Chemistry

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