57282-70-9Relevant academic research and scientific papers
Palladium-Catalyzed Stereoselective Formation of Substituted Allylic Thioethers and Sulfones
Gómez, José Enrique,Guo, Wusheng,Kleij, Arjan W.
, p. 6042 - 6045 (2016)
A general method is reported for the stereoselective preparation of highly functionalized allylic thioethers. This protocol is based on a Pd-catalyzed thiolation of modular vinyl cyclic carbonate substrates and features high (Z)-selectivity, good yields, minimal waste, ample product scope, and operational simplicity. A one-pot strategy was used for the stereoselective formation of pharma-relevant allylic sulfones derived from their in situ prepared thioether precursors.
Highly selective sulfoxidation of allylic and vinylic sulfides by hydrogen peroxide using a flavin as catalyst
Linden, Auri A.,Krueger, Lars,Baeckvall, Jan-E.
, p. 5890 - 5896 (2007/10/03)
A highly chemoselective oxidation of allylic and vinylic sulfides to the corresponding sulfoxides has been developed using flavin 1 as the oxidation catalyst and hydrogen peroxide as the terminal oxidant. The sulfoxides were formed in good to excellent yields in a highly selective manner even when an excess of the oxidant was used. Sulfone formation was completely suppressed to 0.5% (in one single case 1.5% sulfone was detected). No epoxidation of double bonds or interference with other functional groups was observed under the reaction conditions. The general applicability was demonstrated by the selective oxidation of various allylic and vinylic sulfides having different electronic properties. A number of functionalities including hydroxy, acetoxy, amino, silyloxy, and formyl groups are tolerated under these mild reaction conditions.
Process for preparing carotenoid polyene chain compounds and intermediates for preparing the same
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, (2008/06/13)
The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.
A highly efficient chain-extension process in the systematic syntheses of carotenoid natural products
Ji, Minkoo,Choi, Hojin,Park, Minsoo,Kee, Minyong,Jeong, Young Cheol,Koo, Sangho
, p. 3627 - 3629 (2007/10/03)
Successive elongation by a C5 unit is possible when an allylic sulfone is couple with 4-bromo-3-methyl-2-butenyl phenyl sulfide (1). The thiosulfone compound formed was then oxidized to the corresponding disulfone, which, upon coupling with another equivalent of 1 and oxidation, produced the trisulfone 2, again elongated by a C5 unit (see scheme). This process, which can be repeated again, is the basis for a highly efficiently synthesis of carotenoids.
Hydroxythioethers ethyleniques: synthese et rearrangement spontane
Martin, Ghislaine,Sauleau, Jean,David, Michele,Sauleau, Armelle,Sinbandhit, Sourisak
, p. 2190 - 2196 (2007/10/02)
Reactions of vinyloxiranes and thiophenols or phenylthiotrimethyl silane with ZnI2 or nBuLi, at room temperature, were studied.These condensations proceed regio and stereospecifically to afford, in good yields, three families of hydroxy aryl ethylenic sul
STEREOSELECTIVE 1,4-ADDITION OF DIALKYLALUMINUM BENZENETHIOLATE TO VINYL OXIRANES
Yasuda, A.,Takahashi, M.,Takaya, H.
, p. 2413 - 2416 (2007/10/02)
Reactions of vinyl oxiranes and diethylaluminum benzenethiolate in benzene at room temperature proceed regio- and stereoselectively to afford mainly (Z)-4-phenylthio-2-buten-1-ol derivatives in good yields.
