Abstract
The preparation of functionalized 3,5-disubstituted cyclopent-2-enones via a solid-phase sulfone linker strategy is described. Polystyrene/divinylbenzene sulfinate 1 underwent S-alkylation followed by α,α-dialkylation with cis-1,4-dichloro-2-butene to form polymer-bound 3-phenylsulfonylcyclopentenes 8. Subsequent epoxidation of the cyclopentene moiety in 8 was accomplished by treatment of mCPBA, and the resulting oxirane ring in resin 9 was opened with various nucleophiles, i.e., Grignard and cuprate reagents, azide ion, and amines. To complete the sulfone-based linker strategy, Swern or TPAP oxidation of 10 gave a transient γ-ketosulfone, which underwent sulfinate elimination, thus cleaving the sulfone linker. Eleven 3,5-disubstituted cyclopent-2-enones (11) were prepared with this five-step process in 18-40% overall yield from solid-phase benzene sulfinate 1.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4387-4391 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 67 |
| Issue number | 13 |
| DOIs | |
| State | Published - Jun 28 2002 |
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- Organic Chemistry
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The sulfone linker in solid-phase synthesis : Preparation of 3,5-disubstituted cyclopent-2-enones. / Cheng, Wei Chieh; Kurth, Mark J.
In: Journal of Organic Chemistry, Vol. 67, No. 13, 28.06.2002, p. 4387-4391.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The sulfone linker in solid-phase synthesis
T2 - Preparation of 3,5-disubstituted cyclopent-2-enones
AU - Cheng, Wei Chieh
AU - Kurth, Mark J.
PY - 2002/6/28
Y1 - 2002/6/28
N2 - The preparation of functionalized 3,5-disubstituted cyclopent-2-enones via a solid-phase sulfone linker strategy is described. Polystyrene/divinylbenzene sulfinate 1 underwent S-alkylation followed by α,α-dialkylation with cis-1,4-dichloro-2-butene to form polymer-bound 3-phenylsulfonylcyclopentenes 8. Subsequent epoxidation of the cyclopentene moiety in 8 was accomplished by treatment of mCPBA, and the resulting oxirane ring in resin 9 was opened with various nucleophiles, i.e., Grignard and cuprate reagents, azide ion, and amines. To complete the sulfone-based linker strategy, Swern or TPAP oxidation of 10 gave a transient γ-ketosulfone, which underwent sulfinate elimination, thus cleaving the sulfone linker. Eleven 3,5-disubstituted cyclopent-2-enones (11) were prepared with this five-step process in 18-40% overall yield from solid-phase benzene sulfinate 1.
AB - The preparation of functionalized 3,5-disubstituted cyclopent-2-enones via a solid-phase sulfone linker strategy is described. Polystyrene/divinylbenzene sulfinate 1 underwent S-alkylation followed by α,α-dialkylation with cis-1,4-dichloro-2-butene to form polymer-bound 3-phenylsulfonylcyclopentenes 8. Subsequent epoxidation of the cyclopentene moiety in 8 was accomplished by treatment of mCPBA, and the resulting oxirane ring in resin 9 was opened with various nucleophiles, i.e., Grignard and cuprate reagents, azide ion, and amines. To complete the sulfone-based linker strategy, Swern or TPAP oxidation of 10 gave a transient γ-ketosulfone, which underwent sulfinate elimination, thus cleaving the sulfone linker. Eleven 3,5-disubstituted cyclopent-2-enones (11) were prepared with this five-step process in 18-40% overall yield from solid-phase benzene sulfinate 1.
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UR - http://www.scopus.com/inward/citedby.url?scp=0037189250&partnerID=8YFLogxK
U2 - 10.1021/jo0256843
DO - 10.1021/jo0256843
M3 - Article
C2 - 12076132
AN - SCOPUS:0037189250
VL - 67
SP - 4387
EP - 4391
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 13
ER -