New highly strained multifunctional heterocycles by intramolecular cycloadditions of nitrones to bicyclopropylidene moieties

M Marradi, A Brandi, J Magull, H Schill…

Index: Marradi, Marco; Brandi, Alberto; Magull, Joerg; Schill, Heiko; De Meijere, Armin European Journal of Organic Chemistry, 2006 , # 24 p. 5485 - 5494

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Citation Number: 11

Abstract

Abstract Intramolecular cycloadditions of various nitrone functionalities with different substituents (R= Me, Bn, tBu) at the nitrogen atom tethered to a bicyclopropylidene unit through a two-carbon chain led to cis-fused tricyclic isoxazolidines (3-alkyl-3, 3a, 4, 5, 5a, 6- hexahydrocyclopropa [2, 3] cyclopenta [1, 2-c] isoxazolespiro [1, 1′] cyclopropanes) 26 in 42–58% yield with complete regio-and diastereoselectivity. The thermal rearrangement of ...