A convenient synthesis of enantiomerically pure oxindoles using a three component reaction involving 1:3 dipolar cycloaddition reaction has been achieved using solution and solid phase chemistry.
✦ LIBER ✦
Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams
✍ Scribed by Jordi Piró; Mario Rubiralta; Ernest Giralt; Anna Diez
- Book ID
- 104211640
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 92 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of D-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel ® resin, and the lactamisation step was concomitant with the cleavage from the resin.
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