Issue 74, 2023

Organocatalytic (3+3)-cycloaddition of ortho-substituted phenyl nitrones with aryl cyclopropane carbaldehydes: a facile access to enantioenriched 1,2-oxazinanes

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.

Graphical abstract: Organocatalytic (3+3)-cycloaddition of ortho-substituted phenyl nitrones with aryl cyclopropane carbaldehydes: a facile access to enantioenriched 1,2-oxazinanes

Supplementary files

Article information

Article type
Communication
Submitted
15 Jun 2023
Accepted
16 Aug 2023
First published
23 Aug 2023

Chem. Commun., 2023,59, 11133-11136

Organocatalytic (3+3)-cycloaddition of ortho-substituted phenyl nitrones with aryl cyclopropane carbaldehydes: a facile access to enantioenriched 1,2-oxazinanes

A. Hazra, A. Ghosh, N. Yadav and P. Banerjee, Chem. Commun., 2023, 59, 11133 DOI: 10.1039/D3CC02877A

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