Asymmetric borane reduction of prochiral ketone using chiral bis(alpha, alpha-diphenyl-2-pyrrolidinemethanol) carbonate.
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.
Yanagi
Takashi
T
Central Research Laboratories, Kissei Pharmaceutical Co., Ltd, Japan. takashi_yanagi@pharm.kissei.co.jp
Kikuchi
Ken
K
Takeuchi
Hideki
H
Ishikawa
Takehiro
T
Nishimura
Toshihiro
T
Kubota
Minoru
M
Yamamoto
Iwao
I
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
D001880:Boranes; D002254:Carbonates; D011759:Pyrrolidines; D000432:Methanol