Metalation of nonenolizable ketones and aldehydes by lithium dialkylamide bases

CS Shiner, AH Berks, AM Fisher

Index: Shineer, Cristofer S.; Berks, Andrew H.; Fisher, Allison, M. Journal of the American Chemical Society, 1988 , vol. 110, # 3 p. 957 - 958

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Citation Number: 41

Abstract

The carbonyl group can promote bridgehead a-metalation as well as 8-and even y- deprotonations. Upon treatment with base under classical homoenolizationl conditions (eg, t- BuOK/t-BuOH (D), 185-250" C), many nonenolizable ketones undergo H/D exchange, and in some cases rearrangement, via these pathways2 Extensive studies have provided a wealth of mechanistic data, but only a few preparatively useful examples have emerged. 3 More ...