Synthesis of Heterocycle-Substituted Bicyclo[3.1.1]heptanes and Aza-bicyclo[3.1.1]heptanes via Photocatalytic Minisci Reaction
Rebecca I. Revie, Benjamin J. Whitaker, Bhaskar Paul, Russell C. Smith, Edward A. Anderson
Abstract
High Resolution Image Download MS PowerPoint Slide A route toward heterocycle-functionalized bicyclo[3.1.1]heptanes (BCHeps) and aza-bicyclo[3.1.1]heptanes (aza-BCHeps) has been developed, using mild, photocatalytic Minisci-like conditions to introduce various heterocycles at the bridgehead position from readily available N- hydroxyphthalimide esters of the corresponding carboxylic acids. This chemistry enables access to heterocycle-functionalized BCHep-containing structures that are highly relevant in medicinal chemistry research as potential bioisosteres of meta- substituted arenes and pyridines.
Topics & Concepts
Bicyclic moleculeChemistryPhotocatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions