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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp
Paul A Clarke1, William H C Martin, Jason M Hargreaves
1School of Chemistry, University of Nottingham, University Park, Nottingham, Notts, UK NG7 2RD. paul.clarke@nottingham.ac.uk
Abstract:
A one-pot, multi-component reaction for the synthesis of highly substituted tetrahydropyran-4-ones, based on the long forgotten Maitland-Japp reaction has been realised. Two different aldehydes and a derivative of a beta-ketoester can be condensed regioselectively in the presence of a Lewis acid to form tetrahydropyran-4-ones in excellent yields. The diastereoselectively of the reaction was found to be dependant upon the nature of the Lewis acid and the temperature at which the reaction was carried out. This procedure was also extended to the formation of tetrahydropyran-4-ones in greater than 95% enantiomeric excess.
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