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

Abstract

Asymmetric tandem coupling of meso-diols with aldehydes was achieved by using a chiral iridium catalyst. This tandem reaction consists of oxidative desymmetrization of the meso-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.

Key words

aldol reactions - diols - aldehydes - asymmetric catalysis - iridium - tandem reactions

• References


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