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1.5.3 Brook Rearrangement as the Key Step in Domino Reactions

DOI: 10.1055/sos-SD-219-00200

Kirschning, A.; Gille, F.; Wolling, M.Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (20151355.

General Introduction

The Brook rearrangement,[‌1‌‌4‌] named after A. G. Brook (1924–2013), refers to the intramolecular 1,2-anionic migration of a silyl group from carbon to oxygen in α-silylated carbinols 1 in the presence of a catalytic amount of a base or alkali metal (Scheme 1). By deprotonation of the hydroxy group, the migration is accelerated. Occasionally, the reverse process has been reported, which is named the retro-Brook rearrangement. If after silyl migration the newly formed carbanion 2 is trapped by an electrophile other than a proton, Brook rearrangements will become part of a cascade process (Scheme 1).[‌5‌]

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