Article ID Journal Published Year Pages File Type
1390187 Carbohydrate Research 2014 6 Pages PDF
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%.

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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