Oxazaborolidine-catalyzed enantioselective reduction of alpha-methylene ketones to allylic alcohols.
Oxazaborolidine-catalyzed enantioselective reduction of alpha-methylene ketones was efficiently carried out by using borane-diethylaniline as a stoichiometric reducing agent. The combination of this method and subsequent hydrogenation of thus-formed allylic alcohol improved stereoselectivity in the reduction of 24-oxocholesteryl ester to 24-(R)-hydroxycholesteryl ester.
Matsuo
Jun-ichi
J
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp
Kozai
Takaaki
T
Nishikawa
Osamu
O
Hattori
Yu
Y
Ishibashi
Hiroyuki
H
D000814:Aniline Compounds / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D002788:Cholesterol Esters / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D020005:Propanols / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000814:Aniline Compounds; D001372:Aza Compounds; D001880:Boranes; D001896:Boron Compounds; D002788:Cholesterol Esters; D007659:Ketones; D020005:Propanols; C110696:N,N-diethylaniline; C006463:allyl alcohol