Homochiral alpha-D- and beta-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition

Authors
Chiacchio, U Corsaro, A Gumina, G Rescifina, A Iannazzo, D Piperno, A Romeo, G Romeo, R
Citation
U. Chiacchio et al., Homochiral alpha-D- and beta-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition, J ORG CHEM, 64(26), 1999, pp. 9321-9327
Citations number
41
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
26
Year of publication
1999
Pages
9321 - 9327
Database
ISI
SICI code
0022-3263(199912)64:26<9321:HAABV1>2.0.ZU;2-8
Abstract
The introduction of chiral auxiliaries at the C- or N-atom in starting nitr ones has been investigated as a stereoselective synthetic route to heterocy clic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowing an easy and enantioselective synthesis of isoxazolidinyl thymine 26.