@misc{10481/31881,
year = {2014},
url = {http://hdl.handle.net/10481/31881},
abstract = {A novel and efficient synthetic method has been developed for the preparation of alkylated aminopurines (N,N-dimethyl-, 2-chloro-N-methyl-, and N-methyladenines) with achiral and chiral 3,4-dihydro-2H-1,5-benzoxathiepin-3-ol by the Mitsunobu reaction under microwave-assisted conditions. This reaction reveals a complete inversion of the stereogenic centre of the secondary alcohol giving an alkylated purine linked to a homochiral six-membered ring. Fifty novel purine derivatives have been prepared. Alkylation sites have been determined by 2D NMR techniques and for three compounds have been confirmed by X-ray crystallography. The N-9/N-3 regioselectivity can be justified by the electronic effects of the substituents at positions 2 and 6 of the purine.},
organization = {This study was supported by the Instituto de Salud Carlos III (Fondo de Investigación Sanitaria) through the project no.
PI10/00592 and by the ERDF (European Regional
Development Fund). The M. E. G. R. FPU grant AP2007 02954 from the Ministerio de Ciencia e Innovación of Spain is greatly acknowledged. The project "Factoría de Cristalización" Consolider Ingenio 2010 (CSD2006 00015) provided X  ray
structural facilities for this work.},
publisher = {Royal Society of Chemistry},
keywords = {Alkylated aminopurines},
keywords = {Mitsunobu reaction},
keywords = {X-ray crystallography},
title = {Stereospecific alkylation of substituted adenines by the mitsunobu coupling reaction under microwave-assisted conditions},
doi = {10.1039/C4RA01968G},
author = {García Rubiño, María Eugenia and Núñez Carretero, María Del Carmen and Choquesillo Lazarte, Duane and García Ruiz, Juan Manuel and Madrid, Yolanda and Campos Rosa, Joaquín María},
}