Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7nj01395g
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-tetrasubstitu...
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| Main Authors | , |
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| Format | Journal Article |
| Language | English |
| Published |
21.08.2017
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| Online Access | Get full text |
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| Summary: | 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.
2-Adamantyl substituted quinine-squaramide catalyzed aza-Friedel-Crafts reaction of
N
-carbamate isatin ketimines with naphthol afforded chiral isatin-derived 1,3-aminonaphthols with excellent enantioselectivity up to greater than 99% and quantitative yield. |
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| Bibliography: | 10.1039/c7nj01395g Electronic supplementary information (ESI) available. See DOI |
| ISSN: | 1144-0546 1369-9261 |
| DOI: | 10.1039/c7nj01395g |