Copper-Catalyzed Asymmetric Carboboronation of Allenes to Access α-Quaternary Amino Esters with Adjacent Stereocenters

Autor: Chao-Yang Zhao, Hao Zheng, Ding-Wei Ji, Xiang-Ting Min, Yan-Cheng Hu, Qing-An Chen
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Cell Reports Physical Science, Vol 1, Iss 6, Pp 100067- (2020)
Druh dokumentu: article
ISSN: 2666-3864
DOI: 10.1016/j.xcrp.2020.100067
Popis: Summary: Optically active α-quaternary amino acids have received much attention because of the important biomedical applications implicated for compounds containing this structure. Additionally, asymmetric synthesis of highly functionalized chiral α-quaternary amino esters with vicinal stereocenters by a single catalyst is still a great challenge due to the difficulty in stereocontrol of the configurations. Here, we develop a copper-catalyzed highly diastereo- and enantioselective three-component coupling of allenes, diboron, and ketiminoesters to access chiral quaternary amino esters with adjacent stereocenters. The stereochemical control is enabled by using bulky C2-symmetric N-heterocyclic carbene (NHC) as a chiral ligand. This protocol also features mild reaction conditions, wide substrate scope, and may subsequently have diverse applications in organic synthesis.
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