Carboxylate Catalysis: A Catalytic O -Silylative Aldol Reaction of Aldehydes and Ethyl Diazoacetate.

A mild catalytic variant of the aldol reaction between ethyl diazoacetate and aldehydes is described using a combination of N , O -bis(trimethylsilyl)acetamide and catalytic tetramethylammonium pivalate as catalyst. The reaction proceeds rapidly at ambient temperature to afford the O -silylated aldol products in good to excellent yield, and the acetamide byproducts can be removed by simple filtration.