title: Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides.
abstract: Sulfoximines are of considerable interest for incorporation into medicinal compounds. A convenient synthesis of N-protected sulfoximines is achieved, under mild conditions, by rhodium-catalyzed transfer of carbamates to sulfoxides. The first examples of 4-membered thietane-oximines are prepared. Sulfoximines bearing Boc and Cbz groups are stable to further cross coupling reactions, and readily deprotected. This method may facilitate the preparation of NH-sulfoximines providing improved (global) deprotection strategies, which is illustrated in the synthesis of methionine sulfoxide (MSO).
authors.affiliation: †Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom.|‡Department of Pharmacy-Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, Bari 70125, Italy.
authors.forename: Marina
authors.initials: M
authors.lastname: Zenzola
authors.affiliation: †Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom.
authors.forename: Robert
authors.initials: R
authors.lastname: Doran
authors.affiliation: ‡Department of Pharmacy-Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, Bari 70125, Italy.
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
authors.affiliation: †Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom.
authors.forename: James A
authors.initials: JA
authors.lastname: Bull
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008717:Methionine Sulfoximine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D002219:Carbamates; D013454:Sulfoxides; D008717:Methionine Sulfoximine; D012238:Rhodium