Reactions of ethyl 2-acetyl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate and 4-acetylamino-2-oxabicyclo[3.3.0]oct-7-en-3-one with some electrophiles

Abstract

The amide 3 reacted with various electrophilic reagents to give the addition products 5–9; reaction of 3 with m-chloroperoxybenzoic acid (MCPBA) gave the epoxide 10; similarly, the lactone 4(an isomer of 3) reacted extremely selectively with a variety of electrophiles to give a range of polyfunctionalised bicyclic systems 12–15: reaction with MCPBA gave the epoxide 16 as the major product.