Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 1-2, Pages 211-222Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505323
Keywords
amino acids; asymmetric catalysis; carbohydrate synthesis; dihydroxyacetone; ketoses; proline derivatives
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A direct de novo synthesis of ketoses and amino sugars by amino acid-catalyzed asymmetric aldol, Mannich and Michael reactions with dihydroxyacetone phosphate mimics as donors is presented. Proline, proline derivatives and thiazolidine-4-carboxylic acids catalyzed the asymmetric assembly of keto sugars and amino sugars in high yield with up to > 99% ee. The organocatalytic C-3+C-n, methodology presented herein is a direct entry to the de novo synthesis of orthogonally protected C-4, C-5, and C-6 ketoses, carbohydrate derivatives, amino and aza sugars and the total synthesis of polyoxamic acids. The addition of water significantly accelerated and improved the enantioselectivity of the proline-mediated biomimetic asymmetric C-C bond-forming reactions.
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