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4. Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides

F.-L. Haut, C. Habiger, K. Speck, K. Wurst, P. Mayer, J. N. Korber, T. Müller, T. Magauer*

Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophene products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered or moderately reactive substrates to undergo the cycloaddition under mild conditions, thereby increasing the yield by up to 58%. In addition, we showcase its utility by the formal syntheses of the pharmaceuticals NGB 4420 and tenilapine.

Title
4. Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
Author
F.-L. Haut, C. Habiger, K. Speck, K. Wurst, P. Mayer, J. N. Korber, T. Müller, T. Magauer*
Citation
J. Am. Chem. Soc. 2019, 141, 13352−13357
Type
Text