title: Enantioselective hydroarylation of bridged [3.2.1] heterocycles: an efficient entry into the homoepibatidine skeleton.
abstract: Achiral [3.2.1] bridged heterocycles containing a bridging amide can undergo enantioselective hydroarylation reactions under rhodium(I) catalysis. These reactions proceed in high yield and enantioselectivity in most cases, under mild reaction conditions and using commercially available Josiphos ligands. The phosphine ligand structure and the protecting group on the nitrogen both have significant effects on the selectivity and yield of the reactions.
authors.affiliation: CVMED Chemistry, Pfizer Worldwide Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, USA. ryan.brawn@pfizer.com
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Brawn
authors.forename: Cristiano R W
authors.initials: CR
authors.lastname: Guimarães
authors.forename: Kim F
authors.initials: KF
authors.lastname: McClure
authors.forename: Spiros
authors.initials: S
authors.lastname: Liras
mesh_terms: D000577:Amides / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006572:Heterocyclic Compounds, Bridged-Ring; C585357:homoepibatidine; D012238:Rhodium