Issue 38, 2014

Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-d-ribopyranose ring system donors

Abstract

2,3-Dideoxy-D-ribopyranose units are important ring systems found in nature. Herein, we develop a metal-mediated strategy to form this important scaffold featuring a cross-metathesis reaction of the corresponding sugar-derived hydroxyalkene with electron-rich phenyl vinyl sulfide using commercially available ruthenium-catalysts under microwave irradiation as a key step. The final 2,3-dideoxyhexopyranose ring is generated in a single step upon 6-endo electrophilic cyclization.

Graphical abstract: Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-d-ribopyranose ring system donors

Supplementary files

Article information

Article type
Communication
Submitted
25 Feb 2014
Accepted
15 Apr 2014
First published
16 Apr 2014

RSC Adv., 2014,4, 19794-19799

Author version available

Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-D-ribopyranose ring system donors

O. Boutureira, M. Isabel Matheu, Y. Díaz and S. Castillón, RSC Adv., 2014, 4, 19794 DOI: 10.1039/C4RA01668H

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