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Issue 79, 2013
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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)

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Abstract

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.

Graphical abstract: [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)

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Publication details

The article was received on 04 Jul 2013, accepted on 31 Jul 2013 and first published on 01 Aug 2013


Article type: Communication
DOI: 10.1039/C3CC45002C
Citation: Chem. Commun., 2013,49, 8961-8963
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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)

    L. Gao, J. Lu, Z. Song, X. Lin, Y. Xu and Z. Yin, Chem. Commun., 2013, 49, 8961
    DOI: 10.1039/C3CC45002C

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