Me2(CH2CH)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

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Me₂(CH₂CH)SiCN: a bifunctional ethylene equivalent for Diels–Alder reaction based controllable tandem synthesis†

Wen-Biao Wu,^a Bo-Shuai Mu,^a Jin-Sheng Yu

*^ab and Jian Zhou

^abc

Author affiliations

* Corresponding authors

^a 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
E-mail: jsyu@chem.ecnu.edu.cn

^b Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China

^c 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.

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Article information

DOI: https://doi.org/10.1039/D2SC00147K
Article type: Edge Article
Submitted: 09 Jan 2022
Accepted: 24 Feb 2022
First published: 24 Feb 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2022,13, 3519-3525

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Me₂(CH₂CH)SiCN: a bifunctional ethylene equivalent for Diels–Alder reaction based controllable tandem synthesis

W. Wu, B. Mu, J. Yu and J. Zhou, Chem. Sci., 2022, 13, 3519 DOI: 10.1039/D2SC00147K

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