Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5221637 | Tetrahedron | 2010 | 10 Pages |
Abstract
The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to α-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Gaëlle Fourrière, Nathalie Van Hijfte, Jérôme Lalot, Guy Dutech, Bruno Fragnet, Gaël Coadou, Jean-Charles Quirion, Eric Leclerc,