title: Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations.
abstract: The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.
authors.affiliation: AstraZeneca Pharmaceuticals, Alderly Park, Macclesfield, UK.
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Brewster
authors.forename: Simon
authors.initials: S
authors.lastname: Broady
authors.forename: Catherine E
authors.initials: CE
authors.lastname: Davies
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Heightman
authors.forename: Stephen A
authors.initials: SA
authors.lastname: Hermitage
authors.forename: Mark
authors.initials: M
authors.lastname: Hughes
authors.forename: Mark G
authors.initials: MG
authors.lastname: Moloney
authors.forename: Gordon
authors.initials: G
authors.lastname: Woods