title: A novel and expeditious approach to unusual spirolactam building blocks.
abstract: A rapid access to 7-azaspiro[4.5]decan-6-ones 1 involving three regio- and chemoselective reactions starting from tetrabromonorbornyl derivatives is described. The alkaline H(2)O(2) cleavage reaction of monosubstituted alpha-diketones 9 furnished the potential bridged bicyclic lactones 10in a highly regio- and stereoselective manner. The radical-mediated, intermolecular bridgehead C-C bond formation of the versatile bridged lactones 10 with acrylonitrile followed by LAH reduction of the adduct 13 intriguingly leads to the formation of novel spirolactam building blocks 1.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India. faiz@iitk.ac.in
authors.forename: Faiz Ahmed
authors.initials: FA
authors.lastname: Khan
authors.forename: Jyotirmayee
authors.initials: J
authors.lastname: Dash