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Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramide

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Abstract

Herein, an illustrative example to synthesize chiral naphthoxazepine precursors via the aza-Friedel–Crafts reaction of N-alkoxycarbonyl isatin ketimines with naphthol using a new 2-adamantyl-substituted quinine-derived squaramide catalyst is presented; the reaction afforded the chiral-tetrasubstituted 3-amino-2-oxindoles with excellent enantioselectivity of greater than 99% ee and quantitative yields. To the best of our knowledge, this methodology is featured for being representative of the efficiency of sterically hindered hydrocarbon substituents in squaramide organocatalysts in terms of stereoselectivity.

Graphical abstract: Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramide

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Publication details

The article was received on 26 Apr 2017, accepted on 16 Jul 2017 and first published on 17 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01395G
Citation: New J. Chem., 2017, Advance Article
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    Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramide

    S. Karahan and C. Tanyeli, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01395G

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