The stereoselective alkylation and conformational analysis of 14-membered lactones

Abstract

The 14-membered lactone, 13-tetradecanolide, can be alkylated to give mainly the 2R*, 13S*-dimethyltridecanolide. A second alkylation gives the 2,2-dimethyl lactone. The conformation of the starting material and alkylation products exist in the regular [3434] conformation. This model is used to rationalize the stereochemical outcome of the reaction and suggest the conformation of the intermediate enolate.