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Regio- and stereoselectivity of intramolecular nitrile oxide cycloaddition to furan

✍ Scribed by Rita Annunziata; Mauro Cinquini; Franco Cozzi; Laura Raimondi

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 233 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80569-4

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✦ Synopsis

Intramolecular nitrile oxide cycloaddition to functionalized furans occurs with complete regiochemical control but low diastereoselectivity. The poor reactivity of furan as 2 3Z component in the 1,3-dipolar cycloaddition with nitrile oxide' greatly limited its practical use in this reaction. 2,3 This is particularly unfortunate since the furan-nitrile oxide cycloaddition definitely offers the best entry to C-4 oxygenated isoxazolines, and to a number of amino sugars derivatives thereof, as demonstrated by Jager's pioneering work.4 Entropically favoured intramolecular processes 536 could represent an effective alternative to the sluggish intermolecular reaction.

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