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Synlett 2000; 2000(6): 0865-0867
DOI: 10.1055/s-2000-6693
DOI: 10.1055/s-2000-6693
letter
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Indium-Mediated Chain-Extension: An Improved Protocol for the Concise, Diastereospecific Synthesis of KDN and Other Sialic Acids
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/200006/lookinside/thumbnails/10.1055-s-2000-6693-1.jpg)
Aqueous indium-mediated allylation of d-mannose with ethyl 2-(bromomethyl)acrylate leads, under acidic conditions, exclusively to the threo products in high yields. A new purification procedure for indium-mediated reactions has been developed which is based on a simple precipitation of indium-containing phosphate salts. This simplified protocol leads directly to diastereomerically pure KDN and other sialic acids, thus obviating the need for the usual lengthy purification procedures.
allylation - Barbier-type reactions - diastereoselectivity - indium - stereoselective synthesis