Stereoselective Hydrosilylation of 1,2‐Diketones Catalyzed by Chiral Frustrated Lewis Pairs
Ting Liu, Wei Meng, Xiangqing Feng, Haifeng Du
Abstract
Abstract 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 PhSiH 3 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.
Topics & Concepts
HydrosilylationStereoselectivityFrustrated Lewis pairCatalysisEnantioselective synthesisChemistryLewis acids and basesVicinalStereochemistryOrganic chemistryOrganoboron and organosilicon chemistryBoron Compounds in ChemistryChemical Synthesis and Reactions