A simple method of preparing trimethylsilyl- and tert-butyldimethylsilyl-enol ethers of α-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs

Abstract

A simple method of preparing trimethylsilyl- and tert-butyldimethylsilyl-enol ethers of various esters of .alpha.-diazoacetoacetic acid is described. Displacement reaction of 4-acetoxyacetidinone with tert-butyldimethylsilylenol ethers, followed by desilylation, afforded the key chiral precursor for the synthesis of thienamycin analogs [potential antibiotics].