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

A green
protocol has been developed for the synthesis of β-hydroxyl-α-vinyl
carboxylic esters using aldehydes and α,β-unsaturated
esters bearing an activated γ proton as starting materials under
Morita–Baylis–Hillman (MBH) reaction conditions. Diverse
β-hydroxyl-α-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.