Institute of Organic Chemistry, Faculty of Chemistry , Lodz University of Technology , Zeromskiego 116 , 90-924 Łódź , Poland.
J Org Chem. 2018 May 4;83(9):5019-5026. doi: 10.1021/acs.joc.8b00170. Epub 2018 Apr 17.
This study demonstrates an unprecedented reactivity of 2-substituted-1,4-naphthoquinones. By applying the principle of vinylogy, they have been employed as vinylogous pronucleophiles in the organocatalytic cascade reaction for the first time. This novel catalytic activation of 1,4-naphthoquinones enables access to carboannulated naphthalen-1(4 H)-one derivatives of biological importance. The site-selectivity and stereoselectivity of a process proved possible to control by the proper choice of reaction conditions.
本研究展示了 2-取代-1,4-萘醌前所未有的反应活性。通过应用乙烯基类似物原理，它们首次被用作有机催化级联反应中的乙烯基类似亲核试剂。这种 1,4-萘醌的新型催化活化方法可用于获得具有生物重要性的碳环化萘-1(4H)-酮衍生物。通过选择适当的反应条件，可以控制反应的位点选择性和立体选择性。
