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Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines

Timothy J. Donohoe*, Josť A. Basutto, John F. Bower and Akshat Rathi

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K., Email: timothy.donohoechem.ox.ac.uk

T. J. Donohoe, J. A. Basutto, J. F. Bower, A. Rathi, Org. Lett., 2011, 13, 1036-1039.

DOI: 10.1021/ol103088r (free Supporting Information)



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Abstract

The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to pyridines with a wide range of substitution patterns. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.

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Key Words

Cross-Metathesis, Pyridines, Dess-Martin Oxidation


ID: J54-Y2011-0540