title: Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines.
abstract: We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives. This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theoretical study of the reaction mechanism is also described.
authors.affiliation: Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Kubota
authors.affiliation: Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Watanabe
authors.affiliation: Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Keiichi
authors.initials: K
authors.lastname: Hayama
authors.affiliation: Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Hajime
authors.initials: H
authors.lastname: Ito
mesh_terms: D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004095:Dihydropyridines / Q000737:chemistry; D015394:Molecular Structure; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000928:Antidepressive Agents; D004095:Dihydropyridines; D010880:Piperidines; D011725:Pyridines; D017374:Paroxetine