Synthesis of functionalized pyrrolines via microwave-promoted iminyl radical cyclizations
Organic Letters, 2021•ACS Publications
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.
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.
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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