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
Hauptverfasser: Haut, Franz-Lucas, Habiger, Christoph, Speck, Klaus, Wurst, Klaus, Mayer, Peter, Korber, Johannes Nepomuk, Müller, Thomas, Magauer, Thomas
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b07729