文献类型：期刊文献

英文题名：A General Enantioselective α-Alkyl Amino Acid Derivatives Synthesis Enabled by Cobalt-Catalyzed Reductive Addition

作者：Zhang, Chengxi[1,2];Wu, Xianqing[1,2];Qu, Jingping[1,2];Chen, Yifeng[1,2,3,4]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Frontiers Sci Ctr Materiobiol & Dynam Chem, Key Lab Adv Mat,Feringa Nobel Prize Scientist Join, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China;[4]Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China

年份：2024

卷号：146

期号：38

起止页码：25918

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20243817057992);WOS:【SCI-EXPANDED(收录号:WOS:001312733500001)】；

基金：This work was supported by the National Natural Science Foundation of China (22171079, 22371071, 92356301), Natural Science Foundation of Shanghai (21ZR1480400), Shanghai Municipal Science and Technology Major Project (Grant No.2018SHZDZX03), the Program of Introducing Talents of Discipline to Universities (B16017), Shanghai Sailing Program (23YF1408800), and the Fundamental Research Funds for the Central Universities. The authors thank the Analysis and Testing Center of East China University of Science and Technology for help with NMR and HRMS analysis.

语种：英文

外文关键词：Addition reactions - Catalysis - Enantioselectivity - Fatty acid methyl ester - Synthesis (chemical)

摘要：Enantioenriched unnatural amino acids represent a prevalent motif in organic chemistry, with profound applications in biochemistry, medicinal chemistry, and materials science. Herein, we report a cobalt-catalyzed aza-Barbier reaction of dehydroglycines with unactivated alkyl halides to afford unnatural alpha-amino esters with high enantioselectivity. This catalytic reductive alkylative addition protocol circumvents the use of moisture-, air-sensitive organometallic reagents, and stoichiometric chiral auxiliaries, enabling the conversion of a variety of primary, secondary, and even tertiary unactivated alkyl halides to alpha-alkyl-amino esters under mild conditions, thus leading to broad functional group tolerance. The expedient access to biologically active motifs demonstrates the practicality of this protocol by reducing the number of synthetic steps and enhancing the reaction efficiency.