Thieme Chemistry Journals Awardees – Where Are They Now? Chiral Sulfinamide Ligands and Pd-Catalyzed Asymmetric Allylic Alkylations of Ethyl 2-Fluoroacetoacetate

Abstract

New chiral sulfinamide ligands made from salicylic acids and chiral tert-butanesulfinamide was utilized in Pd-catalyzed asymmetric allylic substitutions of ethyl 2-fluoroacetoacetate, which afforded the fluorinated allyl products with up to 98% yield, 94% ee, and 2.2:1 dr. Both sulfoxide and hydroxyl group on the sulfanilamide ligands are ­crucial for enantiocontrol in the Pd-catalyzed allylic alkylations of ethyl 2-fluoroacetoacetate.