Me 2 (CH 2 [double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis.

A bifunctional silyl reagent Me 2 (CH 2 [double bond, length as m-dash]CH)SiCN has been developed as a novel ethylene equivalent for the Diels-Alder (DA) reaction. The use of this reagent enables the controllable synthesis of value-added cyclohexenyl ketones or 2-acyl cyclohexancarbonitrile derivatives through a five- or six-step tandem sequence based on a Wittig/cyanosilylation/DA reaction/ retro -cyanosilylation/isomerization sequence that involves a temporary silicon-tethered intramolecular DA reaction.