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 language | English (US) |
|---|---|
| Pages (from-to) | 3783-3785 |
| Number of pages | 3 |
| Journal | Journal of Organic Chemistry |
| Volume | 59 |
| Issue number | 14 |
| State | Published - 1994 |
ASJC Scopus subject areas
- Organic Chemistry
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Duffy, J. L., & Kurth, M. J. (1994). A novel intramolecular silyl nitronate cycloaddition route to dihydrofuraldehydes and dihydropyranaldehydes. Journal of Organic Chemistry, 59(14), 3783-3785.