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Tuning the Stereoselectivity in One‐Pot Scission/Addition Processes: Synthesis of Azanucleotide Analogues from Proline Derivatives
Author(s) -
MiguélezRamos Javier,
Batchu Venkateswara Rao,
Boto Alicia
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201443
Subject(s) - chemistry , stereoselectivity , diastereomer , proline , decarboxylation , stereochemistry , bond cleavage , chiral auxiliary , organic chemistry , amino acid , catalysis , enantioselective synthesis , biochemistry
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.