Regioselective Hydrosilylation of Propargylic Alcohols: An Aldol Surrogate


  • We thank the National Science Foundation and the National Institutes of Health, General Medical Science (GM-13598), for their generous support of our programs. Z.T.B. is a Stanford Graduate Fellow. Mass spectra were provided by the Mass Spectrometry Regional Center of the University of California–San Francisco supported by the NIH Division of Research Resources.


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Aldol products from a non-aldol reaction: A one-pot protocol effects hydrosilylation of propargyl alcohols and subsequent oxidative cleavage to yield β-hydroxy ketones in a chemo-, regio-, and enantioselective fashion. Further structural elaboration of the intermediate γ-hydroxyvinylsilane is possible before the carbonyl group is unmasked (see scheme).