Abstract
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-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1401-1407 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 40 |
| Issue number | 8 |
| DOIs | |
| State | Published - 1984 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Posner, G. H., Frye, L. L., & Hulce, M. (1984). Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones. Tetrahedron, 40(8), 1401-1407. https://doi.org/10.1016/S0040-4020(01)82425-X