Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1390187 | Carbohydrate Research | 2014 | 6 Pages |
Abstract
•Tandem Staudinger/aza-Wittig reaction of a 1-azidosaccharide derivatives with amines.•Chiral bifunctional saccharide–urea catalysts were used.•An enantioselective Morita–Baylis–Hillman reaction is described.•Enantioselectivity was measured by HPLC.
Chiral ureas containing glycosyl and diphenylphosphinyl scaffolds were found to be an effective organocatalyst. They were synthesised in high yields by a one-pot tandem Staudinger/aza-Wittig coupling reaction. The first attempts of using them in asymmetric synthesis are presented. Yields of the Morita–Baylis–Hillman reaction were moderate with an enantiomeric excess of up to 80%.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Stanisław Porwański,