Organo-Catalyzed Regio- and Geometry-Specific Construction of beta-Hydroxyl-alpha-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications

摘要

A green protocol has been developed for the synthesis of beta-hydroxyl-alpha-vinyl carboxylic esters using aldehydes and alpha,beta-unsaturated esters bearing an activated gamma proton as starting materials under Morita-Baylis-Hillman (MBH) reaction conditions. Diverse beta-hydroxyl-alpha-vinyl carboxylic esters have been synthesized regiospecifically in moderate to good yields with only E geometric selectivity. Other remarkable features include atom efficiency, environmental benignancy, and mild reaction conditions. Furthermore, the reaction products could be readily converted into tetrahydrofuran, dihydrofuran, and furan derivatives.