Hemming, Karl, O'Gorman, P.A. and Page, Michael I. (2006) The synthesis of azabicyclo[4.2.1]nonenes by the addition of a cyclopropenone to 4-vinyl substituted 1-azetines-isomers of the homotropane nucleus. Tetrahedron Letters, 47. pp. 425-428. ISSN 0040-4039
Abstract

The conversion of 4-vinyl substituted β-lactams into 4-vinyl substituted 1-azetines and their subsequent reaction with diphenylcyclopropenone (DPP) results in the formation of a highly functionalised 7-azabicyclo[4.2.1]nonene. This heterocyclic system is an isomer of the homotropane (9-azabicyclo[4.2.1]nonene) nucleus, which is the core structure of a class of alkaloid natural products that includes anatoxin-a. The key processes involved are two ring expansions, one of which constitutes a formal [3+2] cycloaddition and the other of which is an unusual aza-Cope (amino-Claisen) [3,3]-sigmatropic rearrangement.

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