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Diastereoselective self-condensation of dihydroxyfumaric Acid in water: potential route to sugars
Authors:Naidu Sagi Vasudeva  Karri Phaneendrasai  Hu Fang  Krishnamurthy Ramanarayanan
Institution:Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) http://www.scripps.edu/krishnamurthy/
Abstract: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. This transformation exemplifies the diverging roles of DHF as a nucleophile (a synthon for α-hydroxyacetyl anion) and an electrophile (an α-carboxyglycolaldehyde equivalent).
Keywords:diastereoselectivity  dihydroxyfumaric acid  dimerization  NMR spectroscopy  umpolung
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