[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)

Artigo Revisado por pares

[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)

2013; Royal Society of Chemistry; Volume: 49; Issue: 79 Linguagem: Inglês

10.1039/c3cc45002c

ISSN

1364-548X

Autores

Lu Gao, Ji Lu, Zhenlei Song, Xinglong Lin, Yongjin Xu, Zhiping Yin,

Tópico(s)

Coordination Chemistry and Organometallics

Resumo

An unusual [1,5]-Brook rearrangement of the lithium alkoxide of geminal bis(silyl) homoallylic alcohol is described. The unique steric and electronic effects of geminal bis(silane) were found to be crucial for promoting this long-range silyl migration, as well as for facilitating the subsequent γ/Z-selective addition of silyl allyllithium with carbonyl compounds to synthesize diverse configurationally defined Z-vinylsilanes.

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[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)