title: Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control.
abstract: Utilising the propensity of the 2-furanyl group to facilitate equilibration of an adjacent tosylamide chiral centre, a diastereoselective route to 2,6-syn-piperidines was developed that proceeds with high levels of thermodynamic stereocontrol. X-ray crystallography structures suggest that, as seen in similar systems, pseudo-allylic strain between the N-tosyl group and the substituents at the 2 and 6 positions dominates stereochemical preference, overriding 1,3 diaxial interactions.
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. mo263@cam.ac.uk
authors.forename: Matthew
authors.initials: M
authors.lastname: O'Brien
authors.forename: Andrew
authors.initials: A
authors.lastname: Leach
authors.forename: Roly J
authors.initials: RJ
authors.lastname: Armstrong
authors.forename: Keting
authors.initials: K
authors.lastname: Chong
authors.forename: Ross
authors.initials: R
authors.lastname: Sheridan
mesh_terms: D000588:Amines / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000588:Amines; D005663:Furans; D010880:Piperidines; C039281:furan