ol702475e_si_002.pdf (958.33 kB)
Carbonylation of Epoxides to Substituted 3-Hydroxy-δ-Lactones
journal contribution
posted on 2007-12-20, 00:00 authored by John W. Kramer, Daniel Y. Joh, Geoffrey W. CoatesSubstituted 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
carbonylation reaction using in situ IR spectroscopy, and we propose a mechanism that is consistent with previously studied epoxide
carbonylation systems.