Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 5, Pages 846-852Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201443
Keywords
Sequential processes; Synthetic methods; Substitution effects; Nucleotides; Amino acids; Diastereoselectivity
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Funding
- Spanish Plan Nacional de Investigacion Cientifica, Desarrollo e Innovacion Tecnologica, Ministerio de Ciencia e Innovacion (currently Economia y Competitividad
- Research Program) [CTQ2009-07109]
- European Funds for Regional Development (FEDER)
- 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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