Synthesis of Arylzinc Thiolates Containing Perfluoroalkyl Chains. Model Catalyst Precursors for the Enantioselective Zinc-Mediated 1,2-Addition of Dialkylzincs to Aldehydes in Fluorous Biphase Systems

Abstract

The synthesis of perfluoroalkyl-functionalized arene trimethylsilyl ethers and their conversion to ethylzinc thiolates is described. These compounds have been successfully applied as catalysts in the enantioselective addition of diethylzinc to benzaldehyde. This is the first example of a two-phase organic/perfluorous enantioselective catalytic system.