856409-67-1Relevant academic research and scientific papers
Studies on Instructive Construction of exo-Olefin Terminated Five- and Six-Membered Nitrogen Heterocycles: SmI2-Mediated Intramolecular Cyclization of Haloalkynals
Takahashi, Kazunori,Fukushima, Kei,Seto, Marina,Togashi, Azusa,Arai, Yuichi,Tsubuki, Masayoshi,Honda, Toshio
, p. 10636 - 10645 (2018)
Stereoselective construction of exo-olefin terminated pyrrolidine and piperidine frameworks was developed by employing SmI2-mediated intramolecular radical cyclization of haloalkynaks. The radical cyclization affording 2,3-disubstituted pyrrolidines and piperidines proceeded in a highly stereoselective manner. However, decreasing stereoselectivety was observed in the preparation of 2,4-disubstituted pyrrolidine and 3,4-disubstituted piperidine derivatives in the cyclization.
Enantioselective nickel-catalyzedanti-arylmetallative cyclizations onto acyclic electron-deficient alkenes
Gillbard, Simone M.,Green, Harley,Argent, Stephen P.,Lam, Hon Wai
supporting information, p. 4436 - 4439 (2021/05/10)
Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are described.
Synthesis and Formation Mechanism of a Compound with an Unprecedented Skeleton: Dodecahydro-4,10:5,9-diepoxydipyrrolo[3,4-b:3′,4′-f][1,5]diazocine
Shinoda, Misaki,Morita, Nobuyoshi,Tanaka, Kosaku,Hashimoto, Yoshimitsu,Ban, Shintaro,Tamura, Osamu
, p. 1238 - 1243 (2020/12/18)
The reaction of N-(2-{[(tert-butyldimethylsilyl)oxy]imino}ethyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide (6b) with BF3·OEt2 afforded a compound with an unprecedented dodeca-hydro-4,10:5,9-diepoxydipyrrolo[3,4-b:3′,4′-f]
Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling
Shimkin, Kirk W.,Montgomery, John
supporting information, p. 7074 - 7078 (2018/06/04)
Nickel-catalyzed cross-electrophile couplings have recently emerged as highly effective and practical methods for the formation of C-C bonds. By merging this process with well-established π-π coupling chemistry, a new method for the synthesis of tetrasubstituted alkenes has been developed. The procedure relies on the use of chlorosilanes as a means of generating reactive vinylnickel intermediates, which are capable of undergoing a reductive cross-electrophile coupling with alkyl halides. The method not only generates highly substituted allylic alcohol derivatives but also obviates the need for stoichiometric organometallic nucleophiles and provides greatly improved scope and functional group tolerance compared with previously developed methods.
Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes
Shibata, Nina,Tsuchiya, Takahisa,Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Ban, Shintaro,Tamura, Osamu
supporting information, p. 3025 - 3034 (2017/04/10)
ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclizat
Gold-catalyzed intramolecular regio- and enantioselective cycloisomerization of 1,1-bis(indolyl)-5-alkynes
Huang, Long,Yang, Hai-Bin,Zhang, Di-Han,Zhang, Zhen,Tang, Xiang-Ying,Xu, Qin,Shi, Min
supporting information, p. 6767 - 6771 (2013/07/25)
Bis(indole) alkaloids analogues were prepared under mild conditions and in high yields through a gold-catalyzed cycloisomerization of 1,1-bis(indolyl)-5- alkynes (see scheme). The enan Copyright
Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: Remarkable trans-addition of organoboronic reagents
Tsukamoto, Hirokazu,Ueno, Tatsuhiko,Kondo, Yoshinori
, p. 1406 - 1407 (2007/10/03)
Palladium/monophosphine complexes catalyze trans-selective arylative, alkenylative, and alkylative cyclization reactions of alkynals and alkynones with organoboronic reagents. These reactions afford six-membered allylic alcohols with endo-tri- or tetrasub
Mercuric chloride and iodide mediated cyclization of tethered alkynedithioacetals as a general route to five- and six-membered rings: Tuning of regioselectivity by alkyne substitution
Biswas, Goutam,Ghorai, Subir,Bhattacharjya, Anup
, p. 313 - 316 (2007/10/03)
Mercuric chloride mediated cyclization of tethered alkynedithioacetals has been established as a general route to five- and six-membered carbocycles and heterocycles. Substitution at the alkyne terminus leads to preferential formation of five-membered rings, whereas unsubstituted alkynedithioacetals give six-membered rings as the major products. Mercuric iodide interrupts the reaction at the intermediate dithioacetal stage.
Alkynes as synthetic equivalents to stabilized wittig reagents: Intra- and intermolecular carbonyl olefinations catalyzed by Ag(I), BF3, and HBF4
Rhee, Jong Uk,Krische, Michael J.
, p. 2493 - 2495 (2007/10/03)
(Chemical Equation Presented) The first use of cationic silver (AgSbF 4) as a catalyst for intra- and intermolecular alkyne - carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4/
