439901-10-7Relevant academic research and scientific papers
The sulfone linker in solid-phase synthesis: Preparation of 3,5-disubstituted cyclopent-2-enones
Cheng, Wei-Chieh,Kurth, Mark J.
, p. 4387 - 4391 (2002)
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.
Phenylsulfonyl as a directing group for nitrile oxide cycloadditions and mCPBA epoxidations
Butler, Jeffrey D.,Donald, Michael B.,Ding, Zhensheng,Fettinger, James C.,Kurth, Mark J.
scheme or table, p. 5110 - 5112 (2009/12/01)
An unexpected selectivity trend in the nitrile oxide cycloaddition and epoxidation reactions of 4,4-disubstituted cyclopentenes is reported. A variety of facially distinct, 'X-' and 'Y-substituted' cyclopentenes were investigated.
