Article ID Journal Published Year Pages File Type
5285917 Tetrahedron Letters 2006 4 Pages PDF
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.
Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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