Asymmetric diene cyclization/hydrosilylation/oxidation employing 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane

A 1:1 mixture of (NN)Pd(Me)Cl [NN=(R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] (1) and NaBAr4 [Ar=3,5-C6H3(CF3)2] catalyzed the asymmetric cyclization/hydrosilylation of functionalized 1,6-dienes with 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane at −20°C to form silylated cyclopentanes in good yield with up to 95% ee. These silylated carbocycles underwent oxidative cleavage of the CSi bond with H2O2 at room temperature to form the corresponding alcohols.