α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines
Kristen M. Baker, Amanda Tallon, Richard P. Loach, Olivia P. Bercher, Matthew A. Perry, Mary P. Watson
Abstract
A deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to deliver enantiopure α-chiral amines. The success of this method relied on the discovery of a thermally promoted deamination via single-electron transfer of an anion-π complex of the alkylpyridinium cation with potassium carbonate. This method boasts excellent diastereoselectivity over the α-stereocenter as well as broad functional group and heterocycle tolerance.
Topics & Concepts
Enantiopure drugChemistryStereocenterDeaminationPotassium carbonateOrganic chemistryCombinatorial chemistryCatalysisEnantioselective synthesisEnzymeCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisRadical Photochemical Reactions