文献类型：期刊文献

英文题名：Asymmetric Synthesis of α-Alkylated γ-Lactam via Nickel/8-Quinim-Catalyzed Reductive Alkyl-Carbamoylation of Unactivated Alkene

作者：Wu, Xianqing;Shrestha, Mohini;Chen, Yifeng[1]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Front, 130 Meilong Rd, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Sch Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Front, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2021

卷号：32

期号：10

起止页码：955

外文期刊名：SYNLETT

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000614259300001)】；

基金：This work was supported by NSFC/China (21702060), Shanghai Rising-Star Program, Shanghai Municipal Science and Technology Major Project Grant No.2018SHZDZX03) and the Program of Introducing Talents of Discscipline to Universities (B16017), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：8-Quinim; nickel catalysis; reductive coupling; unactivated alkene; dicarbofunctionalization; chiral alpha-alkylated gamma-lactam synthesis

摘要：Chiral-auxiliary-mediated synthesis represents the most frequently used synthetic tool for the induction of chirality on alpha-position of gamma-lactams in organic synthesis. However, the general strategy requires the stoichiometric use of chiral reagents with multiple manipulation steps. Transition-metal-catalyzed asymmetric alkene dicarbofunctionalization using readily available substrates under mild conditions allows the simultaneous construction of two vicinal chemical bonds and a chiral carbon center, hence, gain expedient access to chiral heterocycles. Herein, we disclose a Ni-catalyzed enantioselective reaction of 3-butenyl carbamoyl chloride and primary alkyl iodide enabled by a newly designed chiral 8-quinoline imidazoline ligand (8-Quinim). This protocol features broad functional group tolerance and high enantioselectivities, achieving unprecedented synthesis of chiral nonaromatic heterocycles via catalytic reductive protocol.