biostudies-literatureWu WBFundamental Research Funds for the Central UniversitiesMinistry of Education of the People's Republic of ChinaScience and Technology Innovation Plan Of Shanghai Science and Technology CommissionNational Natural Science Foundation of China3519-3525https://www.ebi.ac.uk/biostudies/studies/S-EPMC8943849biostudies-literatureUnknown13(12)A bifunctional silyl reagent Me<sub>2</sub>(CH<sub>2</sub>[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/<i>retro</i>-cyanosilylation/isomerization sequence that involves a temporary silicon-tethered intramolecular DA reaction.Chemical scienceMe<sub>2</sub>(CH<sub>2</sub>[double bond, length as m-dash]CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis.PMC8943849rdzh202000321N419005002217108720JC141690021725203Wu WBYu JSMu BSZhou JfalseMe<sub>2</sub>(CH<sub>2</sub>[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<sub>2</sub>(CH<sub>2</sub>[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/<i>retro</i>-cyanosilylation/isomerization sequence that involves a temporary silicon-tethered intramolecular DA reaction.2022-01-01T00:00:00Z2022 Mar2025-04-19T16:18:32.038Z2025-04-19T16:18:32.038ZS-EPMC89438493543285510.1039/d2sc00147k