Synthesis of Conjugate and 1,2 Addition Reactions of a Sterically Hindered Allylic Sulfoximine

Article abstract of DOI:10.1016/S0040-4020(01)81928-1

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-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.