Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins
Shang‐Zheng Sun, Yueming Cai, Deliang Zhang, Jia-Bao Wang, Hong-Qing Yao, Xiyan Rui, Rubén Martı́n, Ming Shang
Abstract
Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3–sp3 linkages via sp3 C–N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3–sp3 centers at remote sp3 C–H sites.