Carbonylation of epoxides to substituted 3-hydroxy-α-lactones

Article abstract of DOI:10.1021/ol702475e

Substituted 3-hydroxy-δ-lactones (3HLs) are valuable intermediates in the synthesis of pharmaceuticals and other biologically active natural products. Herein we report the first example of the catalytic carbonylation of substituted homoglycidols to 3HLs using HCo(CO)₄. Upon optimization of the catalyst and reaction conditions, a functionally diverse set of 3HLs was prepared. Mechanistic insight was gained by observation of the carbonyiation reaction using in situ IR spectroscopy, and we propose a mechanism that is consistent with previously studied epoxide carbonyiation systems.