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High-Pressure Promoted Cycloadditions of Enol Ethers and 3-Aryl-2-cyano-2-propenoates

✍ Scribed by René W. M. Aben; René  de Gelder; Hans W. Scheeren

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
147 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis

The high-pressure promoted cycloadditions of enol ethers (1) and alkyl 3-aryl-2-cyano-2-propenoates (2) lead stereoselectively in high yields to 2,6-dialkoxy-4-aryl-3,4-dihydro-2Hpyran-5-carbonitriles (3). These cycloadducts have a high potential for further synthesis due to the presence of various functionalities. This is illustrated with some representative conversions. As reactive cyclic ketene acetals the cycloadducts 3 were easily hydrolyzed to aldehydes (6) or ketones or alcoholized to acetals having additional ester and cyano

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ChemInform Abstract: High-Pressure Promoted Stereoselective Tandem [4 + 2]/[3 + 2] Cycloadditions of Nitroalkenes and Enol Ethers.
✍ R. M. UITTENBOGAARD; J.-P. G. SEERDEN; H. W. SCHEEREN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

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.