Brook rearrangement synthetic utility

Paleo, M. R., Calaza, M. I., Grana, P., Sardina, F. J. Stanna-Brook Rearrangement of Carboxylic Acid Derivatives. Synthetic Utility and Mechanistic Studies. Org. Lett. 2004, 6,1061-1063. 

LInderman, R. J., Ghannam, A. Synthetic utility and mechanistic studies of the aliphatic reverse Brook rearrangement. J. Am. Chem. Soc. 1990,112, 2392-2398. 

In this chapter, we present unique aspects of the rearrangement with a focus on (1) the production of carbanions under mild conditions, (2) the generation of synthetically valuable enol silyl ethers that are often the products, (3) the potential for incorporation of die Brook rearrangement in tandem and sequential anion relay processes, and (4) the utility of the rearrangement in generating chiral, configurationally stable carbanions. 

Brook had set the basis for developing the reaction that came to bear his name, but clearly many mechanistic details remained to be elucidated. In addition, Brook did not anticipate the potential utility of the rearrangement, in fact concluding the 1959 paper with what turned out to be wholly unwarranted self-deprecation It is doubtful whether the rearrangement reported here will have much synthetic application since in general silyl ethers are much more readily prepared than are the corresponding a-silylcarbinols. ... 

---