Bissilyl enal, prepared by a Mannich reaction of 3,3-bissilyl aldehyde with formaldehyde, has proven to be a useful linchpin in an efficient three-component coupling process. The reaction features a [1,4]-Brook rearrangement to generate the silylallyl anion, which adopts a predominant endo-orientation and can undergo addition to electrophiles in a regio- and stereoselective manner, giving various E-vinylsilane species in good yields.
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