title: cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines.
abstract: The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better cis directors than sulfonamides or carbamates) whereas di-N-protected systems gave trans-epoxides (TsNBoc protection gave complete trans stereoselectivity). [structure: see text]
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. paob1@york.ac.uk
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Amanda C
authors.initials: AC
authors.lastname: Childs
authors.forename: Gareth J
authors.initials: GJ
authors.lastname: Ensor
authors.forename: Cheryl L
authors.initials: CL
authors.lastname: Hill
authors.forename: Jonathan P
authors.initials: JP
authors.lastname: Kirby
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Dearden
authors.forename: Sally J
authors.initials: SJ
authors.lastname: Oxenford
authors.forename: Clare M
authors.initials: CM
authors.lastname: Rosser