7787-87-3Relevant articles and documents
Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
Habiger, Christoph,Haut, Franz-Lucas,Korber, Johannes Nepomuk,Müller, Thomas,Magauer, Thomas,Mayer, Peter,Speck, Klaus,Wurst, Klaus
supporting information, (2019/09/06)
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.
Synthesis of Methanethial S-Oxide (Sulfine) and Alkanethial S,S-Dioxides by Fluorodesilylation. Stereochemistry of Their Cyclopentadiene Diels-Alder Adducts
Block, Eric,Wall, Alan
, p. 1425 - 1428 (2007/10/02)
Fluorodesilylation of trimethylsilylmethanesulfinyl chloride 4 in the presence of cyclopentadiene gives 2-thiabicyclohept-5-ene endo-2-oxide, 5; in a like manner 1-trimethylsilylalkanesulfonic anhydrides afford endo- and exo-3-alkyl-2-thiabicyclohept-5-ene 2,2-dioxides, with the endo isomer predominating.Sulfine and alkyl sulfenes are invoked.
