Trimethylsilylketene dialkylacetals in organic synthesis: Reactions with alkyldiazoacetates

Article abstract of DOI:10.1016/S0022-328X(96)06504-7

The reaction of trimethylsilylketene dialkylacetals with alkyldiazoacetates in the presence of Cu(acac)₂ or Rh₂(OAc)₄ results in the formation of alkyl-2,2-dialkoxy-3-trimethylsilylcyclopropane-1-carboxylates 3-8. The cycloaddition proceeds stereoselectively, giving exclusively one of two possible diastereomers. Compounds 4 and 6 are transformed by reaction with LiAlH₄ to cyclopropylmethanols 9 and 10 in high yields. All compounds have been characterized by elemental analyses, ¹H, ¹³C NMR and IR spectroscopy.