Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600 036, India.
Org Biomol Chem. 2021 May 12;19(18):4054-4059. doi: 10.1039/d1ob00416f.
A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this mild method is demonstrated with a wide variety of substrates to furnish pharmaceutically important amidines containing aza-bicyclic and novel aza-tricyclic frameworks in very good yields. A chemoselective reduction of cyclic amidines to 2-/3-azabicyclo[m.n.0]alkanes and octahydroindoles has been developed using a NaBH4/I2 reagent system. The synthetic scope of the chemoselective reduction of the amidine functionality has been exemplified in the stereoselective synthesis of an iminosugar based (±)-epiquinamide analogue.
一种一锅催化方法已经被开发出来，用于通过 CuBr2/K2S2O8 作为有效的单电子转移 (SET) 氧化体系，立体选择性地合成环丙基稠合环状脒。这种温和的方法具有广泛的底物通用性，可以非常好的产率提供含有氮杂双环和新型氮杂三环骨架的具有药物重要性的脒。使用 NaBH4/I2 试剂体系，已经开发出了环状脒的化学选择性还原为 2-/3-氮杂双环[m.n.0]烷和八氢吲哚的方法。通过该脒官能团的化学选择性还原的合成范围已在基于异氨基糖的（±）-epiquinamide 类似物的立体选择性合成中得到了例证。
