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Direct umpolung of glycals and related 2,3-unsaturated N-acetylneuraminic acid derivatives using samarium diiodide.

Authors :
Le TX
Papin C
Doisneau G
Beau JM
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2014 Jun 10; Vol. 53 (24), pp. 6184-7. Date of Electronic Publication: 2014 Apr 24.
Publication Year :
2014

Abstract

The umpolung of glycals with samarium diiodide offers a simple route to novel carbohydrate-derived nucleophilic reagents in a single step using a readily available reductant. The corresponding allyl samarium reagent that arises from the hexose series reacts with ketones at the C3 position with high stereoselectivity; carbon-carbon bond formation takes place only anti to the substituent at the C4 position of the dihydropyran ring. For the sialic acid series, the completely regio- and stereoselective coupling process of the samarium reagent occurs at the anomeric carbon atom and provides a new approach to the α-C-glycosides of N-acetyl neuraminic acid.<br /> (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
53
Issue :
24
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
24764235
Full Text :
https://doi.org/10.1002/anie.201402891