Organic Letters 2010-05-21

Brønsted acid catalyzed asymmetric reduction of ketones and acyl silanes using chiral anti-pentane-2,4-diol.

Jun-Ichi Matsuo, Yu Hattori, Hiroyuki Ishibashi

Index: Org. Lett. 12(10) , 2294-7, (2010)

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Abstract

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.