Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine: synthesis of N-allenylsulfenimides.
Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London, UK. A.Armstrong@imperial.ac.uk
Cooke
Richard S
RS
Shanahan
Stephen E
SE
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D008314:Malonates / Q000737:chemistry*; D008956:Models, Chemical; D013416:Sulfamerazine / Q000138:chemical synthesis* / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*
D000466:Alkadienes; D001388:Aziridines; D008314:Malonates; D013440:Sulfides; C012049:sulfaperine; C008375:mesoxalic acid; D013416:Sulfamerazine