Substrate-Regulated Divergent Addition of <i>N</i>-Sulfonyl Ketimines to Bicyclo[1.1.0]butanes Enabled by Photoinduced Energy Transfer
Shanghui Tian, Ruxue Liu, Kuan Zhang, Yan Xia, Yinuo Liu, Pengfei Li, Xin‐Hua Duan, Li‐Na Guo
Abstract
A substrate-regulated divergent addition of N -sulfonyl ketimines to bicyclo[1.1.0]butanes (BCBs) was developed using a photoinduced energy transfer strategy. The [2π+2σ] cycloaddition of BCBs with saccharin-derived cyclic ketimines yields benzosultam-fused aza-BCHs with good yields and excellent diastereoselectivity. In contrast, reactions of chain N -sulfonyl ketimines with BCBs produce 1,3-fully substituted cyclobutanes via energy-transfer-induced N–S bond homolysis. The ease of large-scale synthesis and derivatizations of products highlight their application potentials.
Topics & Concepts
ChemistryBicyclic moleculeSulfonylSubstrate (aquarium)Energy transferCombinatorial chemistryStereochemistryEnergy (signal processing)Medicinal chemistryOrganic chemistryPhysicsChemical physicsOceanographyAlkylQuantum mechanicsGeologyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions