Rearrangement of 2-azabicyclo[2.2.1]hept-5-en-3-ones: synthesis of cis-3-aminocyclopentane carboxylic acid derivatives

Abstract

The γ-lactam 4 was converted into the bromo ester 6 and the latter compound was transformed in five steps into the diester 10. Similarly the lactam 4 was converted into the hydroxy amide 17via the intermediacy of the dihalogeno compound 11. Compounds 10 and 17 are potential precursors of deoxycarbocyclic nucleosides. Unexpectedly, the lactam 4 furnished the addition product 25 on reaction with benzeneselenenyl bromide and a tentative rationale for the preferred reaction pathway is proposed.