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High pressure promoted tandem [4+2]/[3+2] cycloadditions on the solid phase

✍ Scribed by George J Kuster; Hans W Scheeren

Book ID
104259196
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
210 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 nitroso-acetals. To date, this is the first reported high pressure promoted cycloaddition reaction on a solid support.

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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