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Synthesis and conjugate and 1,2 addition reactions of a sterically hindered allylic sulfoximine

Journal Article


Abstract


  • The synthesis of allylic sulfoximines 3 and 4 is described. The conjugate addition reactions of lithiated 4 with cyclic and acyclic Michael acceptors gives mainly 1,4-γ and 1,4-α adducts respectively in THF and 1,4-α and 1,4-γ adducts respectively in HMPA/THF. The reaction of lithiated 4 and benzaldehyde gives only 1,2-α adducts in THF, however 1,2-α and 1,2-γ adducts were isolated when HMPA/THF was employed as solvent. Benzophenone gave only the 1,2-γ adduct. © 1993.

Publication Date


  • 1993

Citation


  • Pyne, S. G., & Boche, G. (1993). Synthesis and conjugate and 1,2 addition reactions of a sterically hindered allylic sulfoximine. Tetrahedron, 49(37), 8449-8464. doi:10.1016/S0040-4020(01)81928-1

Scopus Eid


  • 2-s2.0-0027327423

Web Of Science Accession Number


Start Page


  • 8449

End Page


  • 8464

Volume


  • 49

Issue


  • 37

Abstract


  • The synthesis of allylic sulfoximines 3 and 4 is described. The conjugate addition reactions of lithiated 4 with cyclic and acyclic Michael acceptors gives mainly 1,4-γ and 1,4-α adducts respectively in THF and 1,4-α and 1,4-γ adducts respectively in HMPA/THF. The reaction of lithiated 4 and benzaldehyde gives only 1,2-α adducts in THF, however 1,2-α and 1,2-γ adducts were isolated when HMPA/THF was employed as solvent. Benzophenone gave only the 1,2-γ adduct. © 1993.

Publication Date


  • 1993

Citation


  • Pyne, S. G., & Boche, G. (1993). Synthesis and conjugate and 1,2 addition reactions of a sterically hindered allylic sulfoximine. Tetrahedron, 49(37), 8449-8464. doi:10.1016/S0040-4020(01)81928-1

Scopus Eid


  • 2-s2.0-0027327423

Web Of Science Accession Number


Start Page


  • 8449

End Page


  • 8464

Volume


  • 49

Issue


  • 37