Stereoselective Hydrosilylation of 1,2-Diketones Catalyzed by Chiral Frustrated Lewis Pairs.

The asymmetric reduction of 1,2-diketones for the synthesis of optically active 1,2-diols, especially 1,2-anti-diols, remains a formidable challenge. In this paper, we describe the first highly stereoselective hydrosilylation of unsymmetrical vicinal diketones with PhSiH3 by using a chiral frustrated Lewis pair (FLP) catalyst, giving a variety of 1,2-diaryl-1,2-anti-diols in high yields with excellent d.r. values and up to 97 % ee. The chiral FLP catalyst exhibits the ability to control regio-, diastereo- and enantioselectivites concurrently.