Me2(CH2[double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis

Wen-Biao Wu; Bo-Shuai Mu; Jin-Sheng Yu; Jian Zhou

doi:10.1039/d2sc00147k

Me₂(CH₂[double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis

Chem Sci. 2022 Feb 24;13(12):3519-3525. doi: 10.1039/d2sc00147k. eCollection 2022 Mar 24.

Authors

Wen-Biao Wu¹, Bo-Shuai Mu¹, Jin-Sheng Yu^{1

2}, Jian Zhou^{1

2

3}

Affiliations

¹ Shanghai 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.
² Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University Haikou 571158 China.
³ Institute of Eco-Chongming Shanghai 202162 China.

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.