Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles
Christian Cristóbal, Daniel Gaviña, Inés Alonso, M. Ribagorda, Juan C. Carretero, Carlos del Pozo, Javier Adrio
Abstract
An enantioselective synthesis of polycyclic fluorinated pyrrolidines has been achieved by Cu-catalyzed intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles. The method displays a wide scope and afforded the desired cycloadducts in high yields with up to 99% ee. These results demonstrate that fluoroalkyl substituents are excellent activating groups in this transformation.
Topics & Concepts
Enantioselective synthesisIntramolecular forceCycloadditionChemistryCatalysisAzomethine ylide1,3-Dipolar cycloadditionCombinatorial chemistryOrganic chemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods