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 |
|---|---|
| Pages (from-to) | 1401-1407 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 40 |
| Issue number | 8 |
| DOIs | |
| State | Published - 1984 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones. / Posner, Gary H.; Frye, Leah L.; Hulce, Martin.
In: Tetrahedron, Vol. 40, No. 8, 1984, p. 1401-1407.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones
AU - Posner, Gary H.
AU - Frye, Leah L.
AU - Hulce, Martin
PY - 1984
Y1 - 1984
N2 - 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.
AB - 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.
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U2 - 10.1016/S0040-4020(01)82425-X
DO - 10.1016/S0040-4020(01)82425-X
M3 - Article
VL - 40
SP - 1401
EP - 1407
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 8
ER -