A general route to α-alkyl (E)-α,β-unsaturated aldehydes

Bis(trimethylsilyl)-tert-butylaldimines 3 react with aldehydes in the presence of zinc bromide at room temperature to give, after hydrolysis, the desired α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity. The reaction was believed to proceed via the α-silyl β-siloxyimines 4.

The bisilyated reagents 3 react with aldehydes to give α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity.Figure optionsDownload as PowerPoint slide