Synthesis of Functionalized Pyrrolines via Microwave-Promoted Iminyl Radical Cyclizations
2021
Singh, Jatinder | Nickel, Garrison A. | Cai, Yu | Jones, Dakota D. | Nelson, Tanner J. | Small, Jeshurun E. | Castle, Steven L.
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 undergo a tandem cyclization–thiyl radical β-elimination, affording terminal alkenes. The cyclizations exhibit a broad scope, and in some cases they are highly diastereoselective. The pyrroline adducts are versatile intermediates that can be transformed into a range of different species.
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