✦ LIBER ✦
Study of the kinetic resolution of (±)-10-exo-hydroxy-pentacyclo[6.2.1.13,6.02,7.05,9]dodeca-4-one by lipase catalysis and the intramolecular racemization of the pure enantiomer by thermal dyotropic reaction
✍ Scribed by José E.D. Martins; João Alifantes; Adriana R. Pohlmann; Valentim E.U. Costa
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 226 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
In this work, the modified synthesis of (±)-10-exo-hydroxy-pentacyclo[6.2.1.1 3,6 .0 2,7 .0 5,9 ]dodeca-4-one (±)-10 as well as its resolution by lipase-catalyzed transesterification with vinyl acetate is described. A thermal racemization process of (+)-10 to (±)-10 was observed. A mechanism involving racemization of (+)-10 through dyotropic intramolecular hydrogen migration is proposed and supported by computational analysis.