214207-23-5Relevant academic research and scientific papers
Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 1953 - 1969 (2005)
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI 2/HMPA or SmI2/DMPU-mediated reductive elimination, 1,2-di-, tri- and tetrasubstituted olefins in moderate to good yields and E/Z selectivity. The conditions are mild and the procedure is widely applicable. The reaction mechanism was studied and a general model, describing the reaction selectivity, is proposed.
A sulfoxide version of the Julia-Lythgoe olefination: A new method for the synthesis of olefins from carbonyl compounds and sulfoxides with carbon-carbon coupling
Satoh, Tsuyoshi,Hanaki, Noriko,Yamada, Noriko,Asano, Tohru
, p. 6223 - 6234 (2007/10/03)
Reaction of β-mesyloxy (or acetoxy) sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and carbonyl compounds in two steps, with alkylmetals (n-BuLi, t-BuLi, or EtMgBr) at low temperature gave olefins in good to excellent yields. When the β-hydroxy sulfoxides derived from arylaldehydes were treated with mesyl chloride in the presence of triethylamine, the sulfoxides directly gave E-olefins in good yields. These reactions offer a sulfoxide version of the Julia-Lythgoe olefination. The reductive vicinal elimination was found to take place through the direct sulfoxide-metal exchange. The stereochemistry of the elimination was investigated and found to be stereospecific; however, the stereospecificity was found to be dependent on the substrates. (C) 2000 Elsevier Science Ltd.
Ligand exchange reaction of sulfoxides in organic synthesis: Sulfoxide version of the Julia-Lythgoe olefination
Satoh, Tsuyoshi,Yamada, Noriko,Asano, Tohru
, p. 6935 - 6938 (2007/10/03)
Reaction of β-mesyloxy sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and aldehydes in two steps, with alkylmetal (n-BuLi, t- BuLi, or EtMgBr) at -78°C gave olefins in good to excellent yields. This reaction offers a sulfoxide version of the Julia-Lythgoe olefination.
