Tetrahedron

X= Y–ZH Systems as potential 1, 3-dipoles. Part 52: Fused-ring forming electrophile induced oxime→ nitrone→ cycloaddition cascades

HA Dondas, R Grigg, S Thibault

Index: Ali Dondas; Grigg, Ronald; Thibault, Sylvie Tetrahedron, 2001 , vol. 57, # 32 p. 7035 - 7045

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Citation Number: 21

Abstract

Electrophile induced cyclisation of oximes onto endocyclic alkenes and exo-methylene cycloalkanes occurs stereo-and regio-specifically generating cis-fused bicyclic nitrones in good yield. Subsequent facially selective cycloaddition with N-methylmaleimide occurs in good yield. The sequence may be carried out as a one-pot procedure and results in the formation of 4 bonds, 2 rings and 6 stereocentres.

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