5464-64-2Relevant articles and documents
N-heterocyclic carbene catalysis: Enantioselective formal [2+2] cycloaddition of ketenes and N-sulfinylanilines
Jian, Teng-Yue,He, Lin,Tang, Cen,Ye, Song
supporting information; body text, p. 9104 - 9107 (2011/10/13)
Sultam of swing: Both enantiomers of 1,2-thiazetidin-3-one oxides were obtained in very good yields with excellent enantioselectivities when using N-heterocyclic carbene catalysts (see scheme; M.S.=molecular sieves, TBS=tert-butyldimethylsilyl). The products were easily converted into 3-oxo-β-sultams, α-mercapto amides, and β-mercapto amines through oxidation or reduction. Copyright
Substituted N-aryl alk-1-enesulfinamides: Preparation, properties and conversion into the corresponding indole compounds [1]
Baudin, Jean-Bernard,Commenil, Marie-Gabrielle,Julia, Sylvestre A.,Lorne, Robert,Mauclaire, Laurent
, p. 329 - 350 (2007/10/03)
Reaction of vinylic organometallic derivatives with N-sulfinyl arenamines 2 affords the title sulfinamides 3. On heating their solutions in selected solvents to 80-124 °C, these sulfinamides are converted into the corresponding indoles 6, probably via a [3.3]-sigmatropic rearrangement to intermediates VIII which undergo an intramolecular carbophilic reaction of the nitrogen atom with the neighboring sulfine group, followed by elimination of HSOH. The triethyloxonium tetrafluoroborate- or boron trifluoride etherate catalyzed conversion 3 → 6 can be carried out at a much lower temperature. Elsevier,.