Organocatalytic (3+3)-cycloaddition of -substituted phenyl nitrones with aryl cyclopropane carbaldehydes: a facile access to enantioenriched 1,2-oxazinanes
The first asymmetric (3+3)-cycloaddition of ortho -substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine catalysts. While the other ortho -substituents gave 1,2-oxazinanes, ortho -hydroxy ones provided a novel class of tetrahydrochromeno-1,2-oxazin...
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| Published in | Chemical communications (Cambridge, England) Vol. 59; no. 74; pp. 11133 - 11136 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Published |
14.09.2023
|
| Online Access | Get full text |
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| Abstract | The first asymmetric (3+3)-cycloaddition of
ortho
-substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine catalysts. While the other
ortho
-substituents gave 1,2-oxazinanes,
ortho
-hydroxy ones provided a novel class of tetrahydrochromeno-1,2-oxazine cores
via
rare 1,3-aryl migration, followed by cyclization. An unusual type of asymmetric approach was also recognized.
The first asymmetric (3+3)-cycloaddition of
ortho
-substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine catalysts. |
|---|---|
| AbstractList | The first asymmetric (3+3)-cycloaddition of
ortho
-substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine catalysts. While the other
ortho
-substituents gave 1,2-oxazinanes,
ortho
-hydroxy ones provided a novel class of tetrahydrochromeno-1,2-oxazine cores
via
rare 1,3-aryl migration, followed by cyclization. An unusual type of asymmetric approach was also recognized.
The first asymmetric (3+3)-cycloaddition of
ortho
-substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine catalysts. |
| Author | Ghosh, Asit Hazra, Arijit Banerjee, Prabal Yadav, Neeraj |
| AuthorAffiliation | Department of Chemistry Lab no-406 Indian Institute of Technology Ropar |
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| ContentType | Journal Article |
| DOI | 10.1039/d3cc02877a |
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| Notes | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2237741 https://doi.org/10.1039/d3cc02877a |
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ortho
-substituted phenyl nitrones with aryl cyclopropane carbaldehydes has been demonstrated by secondary amine... |
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| Title | Organocatalytic (3+3)-cycloaddition of -substituted phenyl nitrones with aryl cyclopropane carbaldehydes: a facile access to enantioenriched 1,2-oxazinanes |
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