Tuning the stereoselectivity in one-pot scission/addition processes: Synthesis of azanucleotide analogues from proline derivatives
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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| Main Authors: | , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Published: |
John Wiley & Sons
2013-02-06
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| Subjects: | Amino acids, Diastereoselectivity, Substitution Effects, Synthetic methods, Sequential Processes, Nucleotides, |
| Online Access: | http://hdl.handle.net/10261/179045 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100003329 http://dx.doi.org/10.13039/501100003339 |
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| Summary: | 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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