160968-45-6Relevant academic research and scientific papers
Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement
Kim, Hanbyul,Jang, Jiwon,Shin, Seunghoon
supporting information, p. 20788 - 20795 (2020/11/27)
A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.
Intramolecular Friedel-Crafts type reaction of vinyloxiranes linked to an ester group
Nagumo, Shinji,Miura, Toshie,Mizukami, Megumi,Miyoshi, Irie,Imai, Masanori,Kawahara, Norio,Akita, Hiroyuki
experimental part, p. 9884 - 9896 (2010/01/16)
The 7-endo Friedel-Crafts cyclization of arylpropyl vinyloxiranes was found to proceed regio- and stereoselectively to afford polyfunctional seven-membered carbocycles in excellent yields.
Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: A diastereoselective entry into octahydrophenanthrenes
Pearson, Anthony J.,Ghidu, Victor P.
, p. 8975 - 8978 (2007/10/03)
A new example is provided of completely diastereoselective polycyclization, affording the octahydrophenanthrene framework. Generation of an iron tricarbonyl stabilized pentadienyl carbocation is the triggering event of the cascade reaction. The carbocation is generated by anchimerically assisted regiospecific protonation of a double bond adjacent to the iron tricarbonyl diene moiety. Tetrafluoroboric acid ether complex appears to be the optimum reagent, affording good yields, even under catalytic conditions.
Pesticidal activity of functionalized alkenes
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Page column 14, (2008/06/13)
The present invention provides non-peptide organic compounds that have a structure analogous to or reminiscent of the TMOF structure and have pesticidal activity. Thus the present invention concerns pesticidal compounds that inhibit digestion in pests by terminating or otherwise blocking synthesis of digestive enzymes by activating a TMOF receptor (collectively referred to herein as “pesticidal compounds”). The pesticidal compounds and other compounds of the present invention are usefully employed in the control of pests, particularly insect pests such as mosquitoes, which ingest blood.
The Geometry of the Carbanionic Moiety Influences the Non-Induced Diastereoselectivity of the -Wittig Rearrangement of Lithiated Diallyl Ethers
Goeppel, Dirk,Muenster, Ingo,Brueckner, Reinhard
, p. 3687 - 3708 (2007/10/02)
Lithiated diallyl ethers with cis- or trans-configuration of the anionic moiety were generated from the diallyl ethers 10, from the vinylogous O,S-acetals 13, and from the O,S-acetals 14 by treatment with nBuLi (in the case of 10) or with lithium naphthal
