Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins
2022
Sun, Shang-Zheng | Cai, Yue-Ming | Zhang, De-Liang | Wang, Jia-Bao | Yao, Hong-Qing | Rui, Xi-Yan | Martin, Ruben | Shang, Ming
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.
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