Visible Light-Triggered and Catalyst- and Template-Free <i>syn</i>-Selective [2 + 2] Cycloaddition of Chalcones: Solid-State Suspension Reaction in Water to Access <i>syn</i>-Cyclobutane Diastereomers
Xianheng Song, Jiayi Gu, Ensheng Zhang, Yi Jiang, Meixiu Xin, Yingfen Meng, Albert S. C. Chan, Yong Zou
Abstract
Light-driven [2 + 2] cycloaddition of olefins is a kind of atom-economic and green transformation for building cyclobutane scaffolds, which are widely found in bioactive compounds and natural products. Although great progress has been made in the (dia)stereoselective synthesis of anti-cyclobutanes by photocycloadditions, the selective synthesis of syn-cyclobutanes is still full of challenges. Herein, we report a visible light-triggered and catalyst- and template-free [2 + 2] cycloaddition strategy of chalcones as a solid-state reaction in water to afford syn-cyclobutanes in high yields with excellent diastereoselectivity.
Topics & Concepts
CyclobutanesCyclobutaneCycloadditionCatalysisDiastereomerChemistryStereoselectivityCombinatorial chemistryPhotochemistryStereochemistryOrganic chemistryRing (chemistry)Radical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods