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Alves Esteves CH, Hall CJJ, Smith PD, et al. Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Org Lett. 2017;19(19):5248-5251doi: 10.1021/acs.orglett.7b02524.
Alves Esteves, C. H., Hall, C. J. J., Smith, P. D., & Donohoe, T. J. (2017). Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Organic letters, 19(19), 5248-5251. https://doi.org/10.1021/acs.orglett.7b02524
Alves Esteves, C Henrique, et al. "Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis." Organic letters vol. 19,19 (2017): 5248-5251. doi: https://doi.org/10.1021/acs.orglett.7b02524
Alves Esteves CH, Hall CJJ, Smith PD, Donohoe TJ. Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Org Lett. 2017 Oct 06;19(19):5248-5251. doi: 10.1021/acs.orglett.7b02524. Epub 2017 Sep 18. PMID: 28920691.
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Org Lett. 2017 Oct 06;19(19):5248-5251. doi: 10.1021/acs.orglett.7b02524. Epub 2017 Sep 18.

Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis.

Organic letters

C Henrique Alves Esteves, Christopher J J Hall, Peter D Smith, Timothy J Donohoe

Affiliations

  1. Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K.
  2. AstraZeneca, Pharmaceutical Sciences , Silk Road Business Park, Macclesfield SK10 2NA, U.K.

PMID: 28920691 DOI: 10.1021/acs.orglett.7b02524

Abstract

A protected pyruvate equivalent is described that allows arylation and arylation/alkylation reactions to be performed at the methyl group. Utilization of the OBO derivative of the pyruvate ester allowed the application of palladium catalyzed arylation reactions together with subsequent 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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