Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 13, Pages 1679-1684Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00475h
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Funding
- National Science Foundation of China [21702035]
- GDUPS
- Pearl River Talents Recruitment Program of Guangdong Province [2017GC010600]
- Science and Technology Program of Guangzhou [201804010455]
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An efficient asymmetric organocatalytic Friedel-Crafts alkylation/hemiketalization/lactonization cascade reaction of 3-ylidene oxindoles with 2-naphthols and activated phenols has been developed. In the presence of 5 mol% of a bifunctional squaramide catalyst, this scalable cascade reaction affords a series of novel furo[2,3-b]benzofuranone derivatives with three adjacent stereogenic centers in good to excellent yields (up to 91%) and with high stereoselectivities (up to 96% ee, >20 : 1 d.r.). Moreover, this cascade reaction provides a distinct lactonization process of amide functional groups under mild reaction conditions to access the diversely decorated furo[2,3-b]benzofuranones of considerable importance to natural product synthesis and medicinal chemistry.
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