Abstract
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.
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