title: Asymmetric borane reduction of prochiral ketone using chiral bis(alpha, alpha-diphenyl-2-pyrrolidinemethanol) carbonate.
abstract: Chiral bis(alpha, alpha-diphenyl-2-pyrrolidinemethanol) carbonate (DPP(2).H(2)CO(3)) is a useful asymmetric auxiliary for the asymmetric borane reduction of prochiral ketones. Chiral DPP(2).H(2)CO(3) is recoverable from the reaction and directly reusable for the reaction. The intermediate of KUR-1246, which we are developing as a new uterine relaxant, was synthesized using the methodology.
authors.affiliation: Central Research Laboratories, Kissei Pharmaceutical Co., Ltd, Japan. takashi_yanagi@pharm.kissei.co.jp
authors.forename: Takashi
authors.initials: T
authors.lastname: Yanagi
authors.forename: Ken
authors.initials: K
authors.lastname: Kikuchi
authors.forename: Hideki
authors.initials: H
authors.lastname: Takeuchi
authors.forename: Takehiro
authors.initials: T
authors.lastname: Ishikawa
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nishimura
authors.forename: Minoru
authors.initials: M
authors.lastname: Kubota
authors.forename: Iwao
authors.initials: I
authors.lastname: Yamamoto
mesh_terms: D001880:Boranes / Q000737:chemistry* / Q000378:metabolism; D002254:Carbonates / Q000737:chemistry / Q000378:metabolism; D000432:Methanol / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D001880:Boranes; D002254:Carbonates; D011759:Pyrrolidines; D000432:Methanol