Tetrahedron letters

Reversal of regiospecificity in the kinetic vs. thermodynamic enolization of bicyclic ketones. Direct bridgehead functionalization of the bicyclo [5.3. 1] undecane ring …

KJ Shea, ST Sakata

Index: Shea, Kenneth J.; Sakata, Steven T. Tetrahedron Letters, 1992 , vol. 33, # 30 p. 4261 - 4264

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Citation Number: 23

Abstract

Abstract In contrast to aliphatic ketones, deprotonation of bicyclo [5.3. 1] undecenone 3 gives the more highly substituted bridgehead enolate under conditions of kinetic control while the less highly substituted enolate is formed under conditions of thermodynamic control. These findings allow for the direct bridgehead functionalization of this important bicyclic skeleton.