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The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp reaction

Clarke, P.A., Martin, W.H.C., Hargreaves, J.M., Wilson, C. and Blake, A.J. (2005) The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp reaction. Organic and Biomolecular Chemistry, 3 (19). pp. 3551-3563. ISSN 1477-0520

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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 -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.

Item Type: Article
Institution: The University of York
Academic Units: The University of York > Chemistry (York)
Depositing User: York RAE Import
Date Deposited: 12 Mar 2009 15:18
Last Modified: 12 Mar 2009 15:18
Published Version: http://dx.doi.org/10.1039/b508252h
Status: Published
Publisher: Royal Society Chemistry
Identification Number: 10.1039/b508252h
URI: http://eprints.whiterose.ac.uk/id/eprint/7119

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