Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.
Org Lett. 2021 May 21;23(10):3970-3974. doi: 10.1021/acs.orglett.1c01148. Epub 2021 May 6.
-Phenyloximes tethered to alkenes undergo 5-- 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.
烯丙基苯并恶唑在微波辐射下发生 5-亚氨基自由基环化反应。所得环状自由基的捕获导致 C-C、C-N、C-O、C-S 或 C-X 键的形成。烯丙基砜经历串联环化-硫自由基β-消除反应，生成末端烯烃。这些环化反应具有广泛的范围，在某些情况下具有高度的非对映选择性。吡咯啉加合物是多功能的中间体，可以转化为一系列不同的物质。
