The sulfone linker in solid-phase synthesis: Preparation of 3,5-disubstituted cyclopent-2-enones

Wei Chieh Cheng, Mark J. Kurth

Research output: Contribution to journalArticle

33 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4387-4391
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number13
DOIs
StatePublished - Jun 28 2002

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Sulfones
divinyl benzene
Cyclopentanes
Ethylene Oxide
Nucleophiles
Epoxidation
Azides
Polystyrenes
Alkylation
Benzene
Amines
Polymers
Resins
Ions
Oxidation
cyclodrine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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 journalArticle

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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.",
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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.

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