title: Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.
abstract: A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation-alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors.forename: Simon
authors.initials: S
authors.lastname: Duttwyler
authors.forename: Colin
authors.initials: C
authors.lastname: Lu
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
authors.forename: Robert G
authors.initials: RG
authors.lastname: Bergman
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011725:Pyridines; D012238:Rhodium