Novel syn intramolecular pathway in base-catalyzed 1,2-elimination reactions of beta-acetoxy esters

Study was conducted to show a new syn intramolecular pathway in the elimination of acetic acid from beta-acetoxy esters and thioesters as a part of a comprehensive investigation of electronic effects on the stereochemistry of based-catalyzed 1,2-elimination reactions. Results show that more acidic thioester substrates do not produce an increased amount of syn stereoselectivity even though their elimination reactions are at the Elcb interface.