Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 9, Pages 5019-5026Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00170
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- National Science Centre, Poland [2015/18/E/STS/00309]
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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(4H)-one derivatives of biological importance. The site-selectivity and stereoselectivity of a process proved possible to control by the proper choice of reaction conditions.
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