- Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
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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 58percent. In addition, we showcase its utility by the formal syntheses of the pharmaceuticals NGB 4420 and tenilapine.
- Habiger, Christoph,Haut, Franz-Lucas,Korber, Johannes Nepomuk,Müller, Thomas,Magauer, Thomas,Mayer, Peter,Speck, Klaus,Wurst, Klaus
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- Synthesis of α,β-unsaturated carbonyl compounds via a visible-light-promoted organocatalytic aerobic oxidation
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α,β-Unsaturated ketones and aldehydes have been synthesized from their corresponding silyl enol ethers in a straightforward protocol involving a visible-light promoted organocatalytic, aerobic oxidation reaction. A cheap organic dye was used catalytically in these reactions as the photosensitizer.
- Zhang, Junlin,Wang, Leming,Liu, Qi,Yang, Zhen,Huang, Yong
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supporting information
p. 11662 - 11664
(2013/12/04)
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- Thermal Rearrangements of 2-Cyclopropylcycloalk-2-enones
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Thermolysis of 2-(2,2-dimethylcyclopropyl)cyclopent-2-enone (2) and 2-cyclopropylcyclohex-2-enone (6) is shown to produce 2-(3-methylbut-2-enylidene)cyclopentanone (10) and 2-propylphenol (14), respectively, via homosigmatropic H-migration and isomerisation.Heating 2-cyclopropylcyclopent-2-enone (8) under a variety of conditions led only to decomposition; no products resulting from vinylcyclopropane - cyclopentene rearrangement were detected.
- Pattenden, Gerald,Whybrow, Derek
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p. 3147 - 3149
(2007/10/02)
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