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High-pressure promoted stereoselective tandem [4+2][3+2] cycloadditions of nitroalkenes and enol ethers

✍ Scribed by RenéM. Uittenbogaard; Jean-Paul G. Seerden; Hans W. Scheeren

Book ID
104208004
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
416 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Tandem [4+2]•[3+2] cycloadditions of nitrostyrene and I-phenyl-2-nitropropene with ethyl vinyl ether or 2,3-dihydrofuran are strongly accelerated under high pressure. Mono 14+2] cycloadducts and tandem [4+21/[3+2] cycloadducts were obtained. Furthermore, the in sttu formed mono adduct reacts selectively with methyl acrylate in a one-pot reaction to give a three-component [4+21/[3+2] cycloadduct. Employing high pressure eliminates the need for stoichiometric amounts of Lewis amd catalysts, large amounts of enol ethers or long reaction times, which are necessary, at ambient pressure.

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High-Pressure Promoted Stereoselective Tandem [4 + 2]/[3 + 2] Cycloadditions of Nitroalkenes and Enol Ethers. -The tandem cycloadditions of the nitroalkenes (I) and (V) with ethyl vinyl ether are found to be strongly accelerated under high pressure. The reactions proceed regioand stereoselectively.

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✍ George J Kuster; Hans W Scheeren 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 210 KB

High pressure was applied tc perform tandem [4+2]/[3+2] cycloadditions of enol ethers with nitrostyrenes and resin-bound acrylate. The s4:ope of this tandem cycloaddition was studied by using building blocks with an increasing substitution pattern, resulting in the formation of highly substituted ni