Study of the kinetic resolution of (±)-10-exo-hydroxy-pentacyclo[6.2.1.13,6.02,7.0 5,9]dodeca-4-one by lipase catalysis and the intramolecular racemization of the pure enantiomer by thermal dyotropic reaction
In this work, the modified synthesis of (±)-10-exo-hydroxy-pentacyclo[6.2.1.13,6.02,7.0 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.
Martins, Jose E. D.,Alifantes, Joao,Pohlmann, Adriana R.,Costa, Valentim E. U.
p. 683 - 688
(2007/10/03)
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