title: A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams.
abstract: A new flexible approach for the stereoselective synthesis of substituted 1H-pyrrol-2(5H)-ones and 3,6-dihydro-1H-pyridin-2-ones has been developed. The general strategy employed the stereoselective reduction of a series of α,β-unsaturated ketones under chelation control to give the corresponding allylic alcohols. Overman rearrangement to install the key C-N bond followed by conversion to either prop-2-enoyl or but-3-enoyl derivatives and a ring closing metathesis reaction gave the target unsaturated γ- and δ-lactams. The synthetic utility of these compounds as building blocks was demonstrated by the preparation of the N-Boc derivative of (-)-coniine.
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ.
authors.forename: Mark
authors.initials: M
authors.lastname: Daly
authors.forename: Kathryn
authors.initials: K
authors.lastname: Gill
authors.forename: Mairi
authors.initials: M
authors.lastname: Sime
authors.forename: Graham L
authors.initials: GL
authors.lastname: Simpson
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007769:Lactams