A One-Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes
James L. Collins, Daryl Staveness, Madison J. Sowden, Corey R. J. Stephenson
Abstract
Detailed herein is the development of a photochemical intermolecular formal [3+2] cycloaddition between cyclopropylimines and substituted alkenes to generate aminocyclopentane derivatives. The Schiff base of the cyclopropylimine was designed to enable a masked N-centered radical approach in which the requisite open-shell character was achieved upon excitation with visible light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via solvolysis and N-acylation. The photochemical component of this reaction sequence was demonstrated to operate in continuous flow.
Topics & Concepts
ChemistryCycloadditionIntermolecular forcePhotochemistryAcylationComponent (thermodynamics)Open shellCombinatorial chemistryMoleculeOrganic chemistryCatalysisThermodynamicsPhysicsRadical Photochemical ReactionsInnovative Microfluidic and Catalytic Techniques InnovationOxidative Organic Chemistry Reactions