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Synfacts 2011(2): 0194-0194
DOI: 10.1055/s-0030-1259240
DOI: 10.1055/s-0030-1259240
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
3,3-Bissilyl Carbonyl and Enol Derivatives via Brook Rearrangement
Z. Song*, Z. Lei, L. Gao, X. Wu, L. Li
Sichuan University, Chengdu and Lanzhou University, P. R. of China
Further Information
Publication History
Publication Date:
19 January 2011 (online)
Significance
The authors disclose a facile and highly stereoselective retro-[1,4] Brook rearrangement of 3-silyl allyloxysilanes. Basic hydrolysis of the (Z)-3,3-bissilyl lithium enolates leads to 3,3-bissilyl carbonyl compounds, while trapping the enolate with electrophiles provides O-substituted (Z)-3,3-bissilyl enol derivatives. These can undergo a Sakurai reaction with aldehydes affording 1,2-diols diastereoselectively.