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Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO 2 : A Shortcut to (S)-(+)-Lavandulol

Yuki Takada, Joaquim Caner, Selvam Kaliyamoorthy, Hiroshi Naka, Susumu Saito

Chemistry. 2017 Dec 19;23(71):18025-18032.

PMID: 28972300

Abstract:

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(-)-carvone by avoiding otherwise necessary protection/deprotection steps.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP58461271-A Lavandulol Lavandulol 58461-27-1 Price
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