Hydrogenolysis of Unstrained Carbon− Carbon σ Bonds: Stereoselective Entry into Benzylic Tertiary Centers

A Wilsily, Y Nguyen, E Fillion

Index: Wilsily, Ashraf; Nguyen, Yen; Fillion, Eric Journal of the American Chemical Society, 2009 , vol. 131, # 43 p. 15606 - 15607

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Citation Number: 30

Abstract

The modification of sp3-hybridized carbon centers through Pd-catalyzed reductive cleavage of unstrained carbon− carbon σ bonds is described. From the hydrogenolysis of benzyl Meldrum's acids bearing an all-carbon benzylic quaternary center, Meldrum's acid and aromatics substituted with a tertiary benzylic stereocenter were obtained in good to excellent yields. Mechanistic studies showed that the reductive cleavage of enantioenriched ...