106734-66-1Relevant articles and documents
Studies on intramolecular alkylation of an α-sulfinyl vinylic carbanion: A novel route to chiral 1-cycloalkenyl sulfoxides
Maezaki, Naoyoshi,Izumi, Mayuko,Yuyama, Sachiko,Sawamoto, Hiroaki,Iwata, Chuzo,Tanaka, Tetsuaki
, p. 7927 - 7945 (2007/10/03)
Intramolecular alkylation of various β-(ω-haloalkyl) substituted vinylic sulfoxides was investigated. Upon treatment with LDA in THF at -78°C, α-sulfinyl carbanion generated from vinylic sulfoxides cyclized at the α-sulfinyl position to give 1-cycloalkenyl sulfoxides with a five- to seven-membered ring. Although iodide or bromide is normally a good leaving group, chloride affords better results than the corresponding iodide and bromide when the reaction takes place at the benzylic position. The cyclization proceeded even with the secondary iodide in moderate yield. Not only the (E)-isomer but also the (Z)-isomer cyclized via rapid inversion of the olefin geometry. No loss of optical purity was observed during isomerization. Various 1-cycloalkenyl sulfoxides including a fused ring and a polyoxygenated rings were synthesized in good to moderate yields. (C) 2000 Elsevier Science Ltd.
Simple and Stereocontrolled Preparation of Optically Pure (E)- and (Z)-1-Alkenyl p-Tolyl Sulfoxides via 1-Alkynyl p-Tolyl Sulfoxides
Kosugi, Hiroshi,Kitaoka, Masaki,Tagami, Katsuya,Takahashi, Akira,Uda, Hisashi
, p. 1078 - 1082 (2007/10/02)
1-Alkynylmagnesium bromides react cleanly and stereospecifically with (-)-menthyl (-)-(S)-p-toluenesulfinate (2) in toluene to produce chiral 1-alkynyl p-tolyl (+)-(S)-sulfoxides 5a-d in high yields.Reduction of 5a-d with lithium aluminum hydride in THF a