Synthesis of Functionalized Pyrrolines via Microwave-Promoted Iminyl Radical Cyclizations

• DOI: 10.1021/acs.orglett.1c01148
• Publication Date: 2021-05-06T18:33:08Z
• Authors: Jatinder Singh; Garrison A. Nickel; Yu Cai; Dakota D. Jones; Tanner J. Nelson; Jeshurun E. Small; Steven L. Castle
• Keywords: Functionalized Pyrrolines; Chemical Sciences not elsewhere classified; Physiology; Biophysics; cyclizations exhibit; trig iminyl; Biochemistry; 01 natural sciences; 5- exo; 0104 chemical sciences; cyclic radicals results; Infectious Diseases; β- elimination; Medicine; pyrroline adducts; Allylic sulfides; microwave irradiation; terminal alkenes; Microwave-Promoted Iminyl Radical C.; Neuroscience; Cancer

O-Phenyloximes tethered to alkenes undergo 5-exo-trig iminyl radical cyclizations upon microwave irradiation. Trapping of the resulting cyclic radicals results in C-C, C-N, C-O, C-S, or C-X bond formation. Allylic sulfides a tandem cyclization-thiyl β-elimination, affording terminal alkenes. The exhibit broad scope, and some cases they are highly diastereoselective. pyrroline adducts versatile intermediates that can be transformed into range different species.