Brønsted acid catalyzed asymmetric reduction of ketones and acyl silanes using chiral anti-pentane-2,4-diol.
Ketones and acyl silanes were reduced to the corresponding alcohols by a simple procedure employing anti-1,3-diol and a catalytic amount (5 mol %) of 2,4-dinitrobenzenesulfonic acid in benzene at reflux. Asymmetric induction reached up to >99% ee when a chiral pentane-2,4-diol of 97% ee was used.
Matsuo
Jun-Ichi
J
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp
Hattori
Yu
Y
Ishibashi
Hiroyuki
H
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D006018:Glycols / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D001557:Benzenesulfonates; D006018:Glycols; D007659:Ketones; D012821:Silanes; C001073:2,4-dinitrobenzenesulfonic acid; C065140:2,4-pentanediol