Science of Synthesis

Ian Fleming, , Science of Synthesis, (2002) 4, 930.

Hydrosilylation of propargyl alcohols ‌17‌ using a variety of catalysts places the silyl group at the terminus (‌Scheme 6‌). The allylic alcohol ‌18‌ could then be oxidized to give an α,β-unsaturated β-silyl aldehyde or ketone ‌19‌, or used as a precursor for the Claisen rearrangement (see Section ‌4.4.41.6‌). If a cationic rhodium catalyst is used for the hydrosilylation, the allylic alcohol can be isomerized at a higher temperature to give the saturated β-silyl ketone ‌20‌ in one operation.[‌30‌] Hydrosilylation of acetals of acrolein, followed by hydrolysis of the acetal group,[‌31‌] or hydrosilylation of allylic alcohol itself, followed by oxidation, gives β-silylpropanals.[‌32‌]

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References

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• 8.Meeeee-Meee, (8888) M 88-8, 888.