Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine

J Org Chem. 2005 Mar 18;70(6):2346-9. doi: 10.1021/jo047940c.

Abstract

[reaction: see text] The asymmetric synthesis and chemical modification of p-bromophenyl methyl sulfoximine (2) is described. Starting from p-bromophenyl menthyl sulfinate (5), enantiopure 2 can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille coupling reactions allow a broad variation of the sulfoximine aryl group, which is otherwise difficult to achieve. The incorporation of a p-morpholino-substituted derivative into a pseudotripeptide demonstrates the applicability of the novel sulfoximine derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Esters / chemical synthesis*
  • Leucine / analogs & derivatives*
  • Leucine / chemical synthesis*
  • Molecular Conformation
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • (S)-gamma-fluoroleucine ethyl ester
  • Esters
  • Palladium
  • Leucine