Journal of the American Chemical Society, Vol.143, No.11, 4154-4161, 2021
Nickel-Catalyzed Enantioselective alpha-Alkenylation of N-Sulfonyl Amines: Modular Access to Chiral alpha-Branched Amines
Chiral alpha-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective alpha-alkenylation of readily available linear N-sulfonyl amines with alkynes to afford a wide variety of allylic amines without the need for exogenous oxidants, reductants, or activating reagents. The method provides a platform for constructing chiral alpha-branched amines as well as derivatives such as alpha-amino amides and beta-amino alcohols, which can be conveniently accessed from the newly introduced alkene. Given the generality, versatility, and high atom economy of this method, we anticipate that it will have broad synthetic utility.