✦ LIBER ✦
Three-Component Domino Knoevenagel/Hetero-Diels–Alder Reaction for the Synthesis of the Amino Sugars 2-Acetoxyforosamine and 2-Acetoxyossamine – Experimental and Theoretical Results
✍ Scribed by Lutz F. Tietze; Simone Dietz; Niels Böhnke; M. Alexander Düfert; Ina Objartel; Dietmar Stalke
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 244 KB
- Volume
- 2011
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
The three‐component domino Knoevenagel/hetero‐Diels–Alder reaction of nitroacetone (6), formaldehyde and ethoxyvinylacetate (4) leads to dihydropyrans 10 and 11, which after hydrogenation of the double bond as well as consecutive reduction of the nitro group and reductive amination give the desired forosamine‐type 2‐acetoxyamino sugars 21–24 and ossamine‐type 25.