An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.本研究开发了一种可用于合成四氢吡喃类化合物的对映选择性交叉脱氢偶联（enantioselective cross-dehydrogenative coupling, CDC）反应。该过程协同实现亲核试剂的原位路易斯酸活化与瞬态氧鎓正离子亲电体的氧化形成，最终得到高效且高对映选择性的CDC反应。此项成果是交叉脱氢偶联反应首次成功应用于非官能化醚的对映选择性偶联反应的典型案例之一。该体系可高效获取存在于多种天然产物与生物活性小分子中的高价值四氢吡喃结构基元。