Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides

J Org Chem. 2015 Jun 19;80(12):6391-9. doi: 10.1021/acs.joc.5b00844. Epub 2015 Jun 2.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Catalysis
  • Methionine Sulfoximine / analogs & derivatives
  • Methionine Sulfoximine / chemical synthesis*
  • Methionine Sulfoximine / chemistry
  • Molecular Structure
  • Rhodium / chemistry*
  • Sulfoxides / chemistry*

Substances

  • Carbamates
  • Sulfoxides
  • Methionine Sulfoximine
  • Rhodium