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 language||English (US)|
|Number of pages||3|
|Journal||Journal of Organic Chemistry|
|State||Published - 1994|
ASJC Scopus subject areas
- Organic Chemistry