P(i-PrNCH2CH2)3N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)

We present an efficient synthesis of beta-hydroxyesters and alpha,beta-unsaturated esters via activation of the silicon-carbon bond of alpha-trimethylsilylethyl acetate using catalytic amounts of the commercially available P(i-PrNCH2CH2)(3)N 1a. Selectivity for either of these two products can be achieved simply by altering the catalyst loading and reaction temperature to afford addition or stereoselective condensation. This method is mild and tolerates a wide array of functional groups.