Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
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-quart...
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| Veröffentlicht in: | Journal of the American Chemical Society 2019-08, Vol.141 (34), p.13352-13357 |
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| container_issue | 34 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 141 |
| creator | Haut, Franz-Lucas Habiger, Christoph Speck, Klaus Wurst, Klaus Mayer, Peter Korber, Johannes Nepomuk Müller, Thomas Magauer, Thomas |
| description | 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. |
| doi_str_mv | 10.1021/jacs.9b07729 |
| format | Article |
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| title | Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides |
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