4.5 Article

Tuning the Stereoselectivity in One-Pot Scission/Addition Processes: Synthesis of Azanucleotide Analogues from Proline Derivatives

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 5, Pages 846-852

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201443

Keywords

Sequential processes; Synthetic methods; Substitution effects; Nucleotides; Amino acids; Diastereoselectivity

Funding

  1. Spanish Plan Nacional de Investigacion Cientifica, Desarrollo e Innovacion Tecnologica, Ministerio de Ciencia e Innovacion (currently Economia y Competitividad
  2. Research Program) [CTQ2009-07109]
  3. European Funds for Regional Development (FEDER)
  4. Consejo Superior de Investigaciones Cientificas (CSIC)

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The one-pot preparation of azanucleotide analogues from proline derivatives has been achieved by a sequential radical decarboxylation/phosphorylation process. The process proceeded under mild conditions, giving high yields of the nucleotide analogues. Remarkably, the stereoselectivity of the reaction can be controlled by using different oxygen and nitrogen substituents at C-4 to give preferentially either the 2,4-cis or 2,4-trans products. In this way, the diastereomeric cis/trans ratio can be shifted from 98:2 to 15:85.

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