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Palladium-catalyzed rearrangement of allylic sulfoximines: Application to the asymmetric synthesis of chiral allylic amines

Journal Article


Abstract


  • The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary 8, 10, 12, 14, 16, 18, and 20, respectively. In the case of the optically active secondary allylic sulfoximines 17 and 19, chiral N-tosyl allylic secondary amines were formed in high enantiomeric purities.

Publication Date


  • 1996

Citation


  • Pyne, S. G., & Dong, Z. (1996). Palladium-catalyzed rearrangement of allylic sulfoximines: Application to the asymmetric synthesis of chiral allylic amines. Journal of Organic Chemistry, 61(16), 5517-5522. doi:10.1021/jo9605105

Scopus Eid


  • 2-s2.0-0000324618

Web Of Science Accession Number


Start Page


  • 5517

End Page


  • 5522

Volume


  • 61

Issue


  • 16

Abstract


  • The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary 8, 10, 12, 14, 16, 18, and 20, respectively. In the case of the optically active secondary allylic sulfoximines 17 and 19, chiral N-tosyl allylic secondary amines were formed in high enantiomeric purities.

Publication Date


  • 1996

Citation


  • Pyne, S. G., & Dong, Z. (1996). Palladium-catalyzed rearrangement of allylic sulfoximines: Application to the asymmetric synthesis of chiral allylic amines. Journal of Organic Chemistry, 61(16), 5517-5522. doi:10.1021/jo9605105

Scopus Eid


  • 2-s2.0-0000324618

Web Of Science Accession Number


Start Page


  • 5517

End Page


  • 5522

Volume


  • 61

Issue


  • 16