Study of the kinetic resolution of (±)-10-exo-hydroxy-pentacyclo [6.2. 1.1 3, 6. 0 2, 7. 0 5, 9] dodeca-4-one by lipase catalysis and the intramolecular racemization of the …

JED Martins, J Alifantes, AR Pohlmann…

Index: Martins, Jose E. D.; Alifantes, Joao; Pohlmann, Adriana R.; Costa, Valentim E. U. Tetrahedron Asymmetry, 2003 , vol. 14, # 6 p. 683 - 688

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Citation Number: 6

Abstract

In this work, the modified synthesis of (±)-10-exo-hydroxy-pentacyclo [6.2. 1.13, 6.02, 7.05, 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.