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 inChemical communications (Cambridge, England) Vol. 59; no. 74; pp. 11133 - 11136
Main Authors Hazra, Arijit, Ghosh, Asit, Yadav, Neeraj, Banerjee, Prabal
Format Journal Article
Published 14.09.2023
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Summary: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.
Bibliography: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
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc02877a