ORGN 757 |
| Carbohydrates are of enormous importance for chemical, biological and medicinal research and play key roles in many biological processes. Many approaches for the de novo synthesis of carbohydrates have been developed, but usually several steps and protecting group manipulations are required. We now present a biomimetic protocol for the direct asymmetric synthesis of carbohydrates. This simple approach succeeds by a proline-catalyzed aldol-reaction of 2,2-dimethyl-1,3-dioxan-5-one as methylene component with different simple aldehydes. Normally good up to excellent chemical yields, anti:syn-ratios of >98:2 and enantiomeric excesses in the area of ee = 90 - ≥98 % are achieved. This new organocatalytic C3+Cn-strategy directly leads to selective protected simple sugars and aminosugars in one step.
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Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
