Synthesis of γ-Haloesters and γ-Ketoesters by Homolytic Addition of Carbon Radicals Generated by α-Haloesters and Triethylborane to Alkenes and Silyl Enol Ethers

Article abstract of DOI:10.1016/S0040-4039(00)77027-4

An efficient synthesis of γ-haloesters has been achieved, under very mild conditions, by addition of electrophilic carbon radicals <*>CH(R)CO2Et (R=H, Me, CO2Et) generated by XCH(R)CO2Et (X=Br, I)/BEt3/air in DMSO to alkenes and cycloalkenes.The synthesis of γ-ketoesters is also possible when silyl enol ethers are used as the substrates.