Enantioselective Multicatalytic Synthesis of α-Benzyl-β-hydroxyindan-1-ones

Abstract

Asymmetric tandem coupling of <i>meso</i>-diols with aldehydes was achieved by using a chiral iridium catalyst. This tandem reaction consists of oxidative desymmetrization of the <i>meso</i>-diol, aldol condensation with an aldehyde, and reduction of the enone intermediate. A one-pot method using an excess of a hydrogen donor gave α-benzyl-β-hydroxyindan-1-ones in up to 94% ee and 88% yield. An asymmetric hydrogen autotransfer method in the absence of an additional hydrogen donor gave the desired benzyl ketone in 92% ee.