Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis
C. Henrique Alves Esteves, Christopher J. J. Hall, Peter D. Smith and Timothy J. Donohoe*
*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K., Email: timothy.donohoechem.ox.ac.uk
C. H. A. Esteves, C. J. J. Hall, P. D. Smith, T. J. Donohoe, Org. Lett., 2017, 19, 5248-5251.
DOI: 10.1021/acs.orglett.7b02524 (free Supporting Information)
A protected pyruvate equivalent allows arylation and arylation/alkylation reactions to be performed at the methyl group. For example, palladium catalyzed arylation reactions of the OBO derivative of the pyruvate ester can be followed by alkylation under basic conditions. Moreover, the OBO protecting group could be easily removed in one step to provide access to a wide range of substituted pyruvate derivatives.
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C. H. A. Esteves, M. Koyioni, K. E. Christensen, P. D. Smith, T. J. Donohoe, Org. Lett., 2018, 20, 4048-4051.