Sequential Pd<sup>0</sup>‐ and Pd<sup>II</sup>‐Catalyzed Cyclizations: Enantioselective Heck and Nucleopalladation Reactions
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Abstract
An enantioselective consecutive cyclization/coupling process, catalyzed by palladium is reported. Stereoinduction arises from an enantioselective carbopalladation, generating an intermediate which promotes a nucleopalladation step. The dual cyclization sequence was compatible with a variety of alkyne-tethered oxygen- and nitrogen-centered nucleophiles, and a variety of alkenyl-tethered aryl iodides, to forge numerous bisheterocycles in good yields and high regio- and enantioselectivities.
Topics & Concepts
Enantioselective synthesisAlkynePalladiumNucleophileChemistryCatalysisArylMedicinal chemistryCombinatorial chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions