Diastereoselective self-condensation of dihydroxyfumaric Acid in water: potential route to sugars |
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Authors: | Naidu Sagi Vasudeva Karri Phaneendrasai Hu Fang Krishnamurthy Ramanarayanan |
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Institution: | Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) http://www.scripps.edu/krishnamurthy/ |
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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). |
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Keywords: | diastereoselectivity dihydroxyfumaric acid dimerization NMR spectroscopy umpolung |
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