Brook rearrangement mediated

Takeda, K., Sawada, Y., Sumi, K. Stereoselective Construction of Eight-Membered Carbocycles by Brook Rearrangement-Mediated [3 + 4] Annulation. Org. Lett. 2002, 4,1031-1033. 

Scheme 6.28 Formation of eight-memhered carhocycles and oxygen-heterocycles via Brook rearrangement-mediated 13+41 annulations.

Scheme 6.44 Stereocontrolled formation of seven- and eight-memhered carbocycles using a comhination of Brook rearrangement-mediated f3+41 annulation and epoxysilane rearrangement...

Chirality transfer from an a-silylalcohol to a-carbamoyloxy- and a-siloxyallyl-carbanions has been investigated using a Brook rearrangement-mediated 5 2 protonation in y-carbamoyloxy- and y-siloxy-ct-silylallyl alcohols. A reaction mechanism that proceeds along one of two pathways that involves a concerted protonation of a silicate intermediate and a concerted lithiation of the intermediate followed by protonation with retention or by protonation after racemization has been proposed. 

The tricyclo[5.3.0.0 " ]decenone ring system (228) has been constructed by reaction of 3-alkyl-3-haloacryloylsilanes (226) with the lithium enolate of 1-acetylcyclopent-l-ene (227) via a Brook rearrangement-mediated 3 - -4-annulation, ... 

Sawada, Y., Sasaki, M., Takeda, K. (2004). Stereoselective construction of eigbt-membered oxygen beterocycles by brook rearrangement-mediated [3 -I- 4] annulation. Organic Letters, 6, 2277-2279. 

Sasaki M, Oyamada K, Takeda K. Formal total syntheses of (-l-)-prelaureatin and (+)-laurallene by diastereoselective Brook rearrangement-mediated [3+4] annulations. J. Org. Chem. 2010 75(ll) 3941-3943. 

K, Takeda K. Diastereoselective Brook rearrangement-mediated [3 + 4] annulation application to a formal synthesis of (+)-laurallene. Org. Lett. 2008 10(9) 1803-1806. 

Indium-mediated allylation of trialkyl(difluoroacetyl)silane 70 in aqueous media gives homoallylic alcohol 71 exclusively (Scheme 60). Both water and THF are essential for the allylation reaction. It is worth noting that homoallylic alcohol 71 is formed exclusively under these reaction conditions. On the contrary, enol silyl ether 72 is a major product of the fluorinated acylsilanes reaction with other organometallic compounds than indium via a Brook rearrangement and defluorination. Indium-mediated allylsilylation of carbonyl compounds provides a facile route to 2-(hydroxyethyl)allylsilanes. The allene homologs are similarly prepared (Scheme 61).244,244a... 

Gandon, V., Bertus, P., Szymoniak, J. New transformations from a 3-silyloxy-2-aza-1,3-diene consecutive Zr-mediated retro-Brook rearrangement and reactions with electrophiles. Tetrahedron 2000, 56, 4467-4472. 

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