双核锌催化剂促进的四氢呋喃螺[吲哚啉-2,3’-吡咯]的不对称催化合成。
Catalytic Asymmetric Synthesis of Tetrahydrofuran Spirooxindoles via a Dinuclear Zinc Catalyst.
机构信息
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, No. 100, Science Road, Zhengzhou, Henan 450000, P. R. China.
School of Chemistry & Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, P. R. China.
出版信息
J Org Chem. 2020 Mar 20;85(6):4195-4206. doi: 10.1021/acs.joc.9b03378. Epub 2020 Mar 3.
An asymmetric Michael/hemiketalization and Fridel-Crafts reaction has been reported through a one-pot reaction. A number of structurally novel tetrahydrofuran spirooxindoles are synthesized in the presence of a 10 mol % dinuclear zinc catalyst with diastereomer ratios (dr) of 3:1-13:1 and an enantiomeric excess (ee) of 75-99%. The reaction can be performed on a gram scale without impacting its efficiency. The absolute configuration of products is confirmed by X-ray single crystal structure analysis, and a possible mechanism is proposed.
通过一锅反应，报道了一种不对称的迈克尔/半缩醛化和傅-克反应。在双核锌催化剂的存在下，通过一锅反应合成了一系列结构新颖的四氢呋喃螺[吲哚啉-3,3′-吡咯烷]。非对映异构体比例(dr)为 3:1-13:1，对映体过量(ee)为 75-99%。反应可以在克级规模下进行，而不会影响其效率。通过 X 射线单晶结构分析确定了产物的绝对构型，并提出了可能的反应机理。
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