Direct Synthesis of Bicyclic Acetals via Visible Light Catalysis
Fengjin Wu, Leifeng Wang, Ying Ji, Ge Zou, Hong C. Shen, David A. Nicewicz, Jiean Chen, Yong Huang
Abstract
Polysubstituted bicyclic acetals are a class of privileged pharmacophores with a unique 3D structure and an adjacent pair of hydrogen bond acceptors. The key, fused acetal functionality is often assembled, via intramolecular cyclization, from linear substrates that are not readily available. Herein, we report a formal cycloaddition between cinnamyl alcohols and cyclic enol ethers under ambient photoredox catalysis conditions. Polysubstituted bicyclic acetals can be prepared in one step from readily available building blocks. Employment of sugar-derived enol ethers allows easy access to a library of scaffolds with intriguing conformation and medicinal chemistry potential.