Carbonylation of epoxides to substituted 3-hydroxy-delta-lactones.
Substituted 3-hydroxy-delta-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.
Kramer
John W
JW
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Joh
Daniel Y
DY
Coates
Geoffrey W
GW
D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D004852:Epoxy Compounds; D007659:Ketones; D007783:Lactones