521275-65-0Relevant academic research and scientific papers
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 (2003)
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.
Highly Efficient and General Synthetic Method of Various Retinyl Ethers
Lee, Jun Sup,Jeong, Young Cheol,Ji, Minkoo,Baik, Woonphil,Lee, Sijoon,Koo, Sangho
, p. 1937 - 1940 (2007/10/03)
Bromination of 4 by PBr3 under Cu(I) catalyst produces the ambidextrous allylic halide 5 regioselectively and stereoselectively. Hetero nucleophiles distinguish the allylic carbon containing Br from the one containing Cl in 5 to give the heteroatom-substituted C5 allylic chloride 3. The Julia olefination reaction with the C15 sulfone 2 provides diverse retinyl ethers 1.
