Diastereoselective Self-Condensation of Dihydroxyfumaric Acid in Water: Potential Route to Sugars

Diastereoselective Self-Condensation of Dihydroxyfumaric Acid in Water: Potential Route to Sugars

Jack of all trades: Water‐soluble salts of DHF underwent self‐condensation to afford the threo diastereomer of pentulosonic acid, through differing reaction pathways contingent on the metal salt used (see scheme). This transformation exemplifies the diverging roles of DHF as a nucleophile (a synthon...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-08, Vol.50 (35), p.8127-8130
Hauptverfasser: Naidu Sagi, Vasudeva, Karri, Phaneendrasai, Hu, Fang, Krishnamurthy, Ramanarayanan
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates - chemistry
diastereoselectivity
dihydroxyfumaric acid
Dimerization
Fumarates - chemistry
Metals - chemistry
NMR spectroscopy
Salts - chemistry
Stereoisomerism
umpolung
Water - chemistry
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Beschreibung
Zusammenfassung:Jack of all trades: Water‐soluble salts of DHF underwent self‐condensation to afford the threo diastereomer of pentulosonic acid, through differing reaction pathways contingent on the metal salt used (see scheme). This transformation exemplifies the diverging roles of DHF as a nucleophile (a synthon for α‐hydroxyacetyl anion) and an electrophile (an α‐carboxyglycolaldehyde equivalent).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201102045