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Formation of functionalized cyclic ethers by intramolecular nitrile oxide cycloadditions

✍ Scribed by Albert Padwa; Ugo Chiacchio; Dennis C. Dean; Allen M. Schoffstall; Alfred Hassner; K.S.K. Murthy

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 259 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80447-5

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✦ Synopsis

The reaction of 0-trimethylsilyl a-bromo aldoximes with unsaturated alcohols produces oximino ethers which can be readily oxidized with sodium hypochlorite. The transient nitrile oxide intermediate formed undergoes spontaneous cyclization affording fused isoxazolines. MM2 calculations help rationalize the observed stereoselectivity. Substituted and functionalized tetrahydrofurans and pyrans are of interest as analogs of carbohydrates.* Recently, we reported the synthesis of a-brominated aldoxime derivatives (1)

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