Abstract

A 4‐methylene‐5‐spirocyclopropane isoxazolidine was prepared with complete regioselectivity through the 1,3‐dipolar cycloaddition reaction of a pyrroline N‐oxide with a cyclopropylidene acetate, followed by reduction and elimination. Thermal rearrangement of the isoxazolidine gives an indolizidinone that retains the exocyclic methylene moiety. The exo‐methylene substituent confers a particular reactivity to this heterocycle; it can undergo thermal hetero‐Diels–Alder cycloadditions and ene reactions with different reaction partners.

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