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Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Shang-Zheng Sun, Yue-Ming Cai, De-Liang Zhang, Jia-Bao Wang, Hong-Qing Yao, Xi-Yan Rui, Ruben Martin and Ming Shang*

*Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China, Email: shangsjtusjtu.edu.cn

S.-Z. Sun, Y.-M. Cai, D.-L. Zhang, J.-B. Wang, H.-Q. Yao, X.-Y. Rui, R. Martin, M. Shang, J. Am. Chem. Soc., 2022, 144, 1130-1137.

DOI: 10.1021/jacs.1c12350


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Abstract

A sterically encumbered bis(oxazoline) ligand backbone enables a Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. This protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization.

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Key Words

alkylation, diethoxymethylsilane


ID: J48-Y2022