期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 34, 页码 13352-13357出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07729
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资金
- Austrian Science Fund FWF [P31023-NBL]
- Center for Molecular Biosciences CMBI
- Tyrolean Science Fund TWF [UNI-0404/2340]
- Austrian Science Fund (FWF) [P31023] Funding Source: Austrian Science Fund (FWF)
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.
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