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Stereoselective One-Pot Synthesis Of Vinylsilanes From Aromatic Aldehydes, Man Lung Kwan, Chiu Yeung, Kerry Breno, Kenneth Doxsee
Stereoselective One-Pot Synthesis Of Vinylsilanes From Aromatic Aldehydes, Man Lung Kwan, Chiu Yeung, Kerry Breno, Kenneth Doxsee
Man Lung Desmond Kwan
Vinylsilanes serve as convenient vinyl anion equivalents, but procedures for their stereoselective synthesis from aldehydes are scarce. A variety of aromatic aldehydes are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to the aldehyde followed by treatment with Cp2TiCH2·AlMe2Cl (‘Tebbe's reagent’). Halide and alkoxide substituents are tolerated, and (E)-vinylsilanes are formed exclusively in good yield.