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Me2(CH2[double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based
Wen-Biao Wu1, Bo-Shuai Mu1, Jin-Sheng Yu1,2
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University Shanghai 200062 China jsyu@chem.ecnu.edu.cn.
Abstract:
A bifunctional silyl reagent Me2(CH2[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.
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