Kumar Rayala Naveen, Lee Seongmin
The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
Molecules. 2024 Dec 9;29(23):5812. doi: 10.3390/molecules29235812.
The hypervalent iodine-mediated formation of steroidal 5/5-spiroiminals and 5/5-spiroaminals from steroidal amines is presented. Under the influence of excess PhI(OAc) and iodine in acetonitrile at 0 °C, steroidal amines smoothly underwent cyclization to give a mixture of 5/5-spiroiminals and 5/5-spiroaminals. This reaction represents the first example of a C-H-activation-mediated formation of a spiroiminal. Presumably, the formation of 5/5-spiroiminals occurs through aminyl radical-mediated cyclization followed by amine-to-imine oxidation.
本文介绍了由甾体胺通过高价碘介导形成甾体5/5-螺亚胺和5/5-螺胺的过程。在过量的醋酸碘苯（PhI(OAc)）和碘的影响下，甾体胺在0℃的乙腈中顺利进行环化反应，生成5/5-螺亚胺和5/5-螺胺的混合物。该反应代表了通过C-H活化介导形成螺亚胺的首个实例。据推测，5/5-螺亚胺的形成是通过氨基自由基介导的环化反应，随后是胺到亚胺的氧化反应。
