Tetrahedron p. 1401 - 1408 (1984)
Update date:2022-08-02
Topics:
Posner, Gary H.
Frye, Leah L.
Hulce, Martin
Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2, proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7.Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7.Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfinyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.
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