Microwave accelerated SN2′ substitution of Baylis–Hillman acetates: A comparative study of conventional heating versus microwave irradiation

Baylis–Hillman acetates undergo a rapid SN2′ allylic substitution with ethyl (triphenyl phosphoranylidene) acetate under microwave irradiation to afford ethyl 5-aryl or alkyl-(E)-pent-4-enoates in high yields with high (E)-stereoselectivity. The reaction rates and yields are significantly improved by employing microwave irradiation. A comparative study under thermal conditions and microwave irradiation is also described.

Graphical abstractBaylis–Hillman acetates undergo a rapid SN2′ allylic substitution with ethyl (triphenyl phosphoranylidene) acetate under microwave irradiation to afford ethyl 5-aryl or alkyl-(E)-pent-4-enoates in high yields. Figure optionsDownload full-size imageDownload as PowerPoint slide