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) |
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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