Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds
Mark Deeprose, Martin A. Lowe, Adam Noble, Kevin I. Booker‐Milburn, Varinder K. Aggarwal
Abstract
The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C-C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.
Topics & Concepts
StereocenterCyclobutanesChemistryCyclobutanePhotocatalysisSteric effectsQuaternary carbonCombinatorial chemistryCatalysisPhotochemistryStereochemistryOrganic chemistryEnantioselective synthesisRing (chemistry)Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques