Transition metal-catalyzed hydrosilylations of carbonyls and alkenes are useful processes for stereoselective synthesis of chiral alcohols and 1,3-diols after subsequent oxidative desilylation.  However, tandem dual hydrosilylations of a,�-unsaturated carbonyl compounds to directly afford oxasilacycles has been underexplored.  We have been developing efficient transition metal-catalyzed chemo-, regio-, and stereoselective one-pot tandem dual hydrosilylations of a,�-unsaturated aldehydes and ketones leading to the 1,3-diols after subsequent Fleming-Tamao oxidation, which are a common structural feature of many bioactive polyketide natural products.  In addition, our understanding for silylene metal dihydride mechanism will be presented.

Studies toward transition metal-catalyzed regio- and stereoselective tandem dual hydrosilylations of a,�-unsaturated aldehydes and ketones: An innovative method for synthesizing 1,3-diols

247th National Meeting (2014)

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