Abstract
A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.
| Original language | English |
|---|---|
| Pages (from-to) | 2307-2314 |
| Number of pages | 8 |
| Journal | Pure and Applied Chemistry |
| Volume | 53 |
| Issue number | 12 |
| DOIs | |
| State | Published - Jan 1 1981 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Chemical Engineering(all)
- Chemistry(all)
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Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides. / Posner, Gary H.; Mallamo, John P.; Miura, Kyo; Hulce, Martin.
In: Pure and Applied Chemistry, Vol. 53, No. 12, 01.01.1981, p. 2307-2314.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides
AU - Posner, Gary H.
AU - Mallamo, John P.
AU - Miura, Kyo
AU - Hulce, Martin
PY - 1981/1/1
Y1 - 1981/1/1
N2 - A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.
AB - A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.
UR - http://www.scopus.com/inward/record.url?scp=0008391388&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0008391388&partnerID=8YFLogxK
U2 - 10.1351/pac198153122307
DO - 10.1351/pac198153122307
M3 - Article
AN - SCOPUS:0008391388
VL - 53
SP - 2307
EP - 2314
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
SN - 0033-4545
IS - 12
ER -