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DOI: 10.1055/sos-SD-219-00200

Kirschning, A.; Gille, F.; Wolling, M.Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (20151356.

1,2-Brook rearrangements require access to α-silyl alkoxides. These compounds can be generated from aldehydes or ketones by nucleophilic addition of silyllithium species, from acylsilanes by addition of nucleophiles, from α-silyl carbinols by deprotonation, and from epoxysilanes if oxirane ring opening occurs at the non-silyl-substituted terminus. Retro-Brook rearrangements are also known, though less common, which unravels the reversibility of these rearrangements. Consequently, the retro-1,2-Brook rearrangement will also be covered in this chapter.