Highly regioselective intramolecular hydroxymethylation of α,β-unsaturated carboxylic acids

Article abstract of DOI:10.1016/0040-4039(96)01931-4

A convenient synthesis of hydroxy esters 7 and lactones 8 by starting from easily available α,β-unsaturated carbocylic acids 4 is described. The key step of this transformation is a hitherto unknown radical cyclization of silyl esters, which exhibits a high degree of regioselectivity through steric and orbital control.