Premium
One‐Pot Synthesis of Azanucleosides from Proline Derivatives – Stereoselectivity in Sequential Processes
Author(s) -
Boto Alicia,
Hernández Dácil,
Hernández Rosendo
Publication year - 2010
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.201000360
Subject(s) - chemistry , stereoselectivity , decarboxylation , benzotriazole , proline , domino , organic chemistry , combinatorial chemistry , nitrogen , amino acid , catalysis , biochemistry
Abstract Common amino acid derivatives can be transformed in one‐step fashion into N ‐azanucleosides. The method is a sequential process initiated by a domino radical decarboxylation/oxidation reaction; an acyliminium ion is formed as an intermediate and can be trapped by nitrogen bases (purines, pyrimidines, and benzotriazole). The mildness of the reaction conditions and the good yields obtained make this procedure an interesting alternative to the conventional processes. Good stereoselectivities were obtained with 4‐(silyloxy)proline derivatives as substrates.