75822-61-6Relevant academic research and scientific papers
Phosphine-Catalyzed Activation of Vinylcyclopropanes: Rearrangement of Vinylcyclopropylketones to Cycloheptenones
Wu, Jun,Tang, Yuhai,Wei, Wen,Wu, Yong,Li, Yang,Zhang, Junjie,Zheng, Yuansuo,Xu, Silong
, p. 6284 - 6288 (2018)
We report a phosphine-catalyzed activation of electron-deficient vinylcyclopropanes (VCPs) to generate an ambident C5 synthon that is poised to undergo consecutive reactions. The utility of the activation is demonstrated in a phosphine-catalyzed rearrangement of vinylcyclopropylketones to cycloheptenones in good yields with a broad substrate scope. Mechanistic investigations support a stepwise process comprising homoconjugate addition, water-assisted proton transfer, and 7-endo-trig SN2′ ring closure.
One-Pot Synthesis of Metastable 2,5-Dihydrooxepines through Retro-Claisen Rearrangements: Method and Applications
Zhang, Wei,Baudouin, Emmanuel,Cordier, Marie,Frison, Gilles,Nay, Bastien
, p. 8643 - 8648 (2019/07/16)
A one-pot methodology to synthesize metastable bicyclic 2,5-dihydrooxepines from cyclic 1,3-diketones and 1,4-dibromo-2-butenes through the retro-Claisen rearrangement of syn-2-vinylcyclopropyl diketone intermediates is reported. DFT calculations were performed to understand the reaction selectivity and mechanisms towards [1,3]- or [3,3]-sigmatropic rearrangements, highlighting the crucial influence of the temperature. The reaction was successfully applied to a short protecting group-free total synthesis of radulanin A, a natural 2,5-dihydrobenzoxepine. Moreover, the strong herbicidal potential of this natural product is demonstrated for the first time.
Recycling Catalyst as Reactant: A Sustainable Strategy to Improve Atom Efficiency of Organocatalytic Tandem Reactions
Wei, Wen,Tang, Yuhai,Zhou, Yan,Deng, Ge,Liu, Ziyu,Wu, Jun,Li, Yang,Zhang, Junjie,Xu, Silong
supporting information, p. 6559 - 6563 (2018/10/20)
A sustainable strategy by internally recycling an organocatalyst as a reactant in a downstream reaction to improve the atom efficiency of organocatalytic tandem reactions is described. Specifically, a one-pot tandem Cloke-Wilson/Boulton-Katritzky reaction
Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
Zhang, Jingfang,Tang, Yuhai,Wei, Wen,Wu, Yong,Li, Yang,Zhang, Junjie,Zheng, Yuansuo,Xu, Silong
supporting information, p. 3043 - 3046 (2017/06/23)
An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in gener
Non-decarbonylative photochemical versus thermal activation of Bu4N[Fe(CO)3(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes
Lin, Che-Hung,Pursley, Dominik,Klein, Johannes E. M. N.,Teske, Johannes,Allen, Jennifer A.,Rami, Fabian,K?hn, Andreas,Plietker, Bernd
, p. 7034 - 7043 (2015/11/17)
The base metal complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the rearrangement of vinyl and arylcyclopropanes both under thermal or photochemical conditions to give the corresponding vinyl or aryldihydrofurans in good to excellent yi
Domino [3+3] annulation/ring-cleavage reactions of 1,3- bis(trimethylsilyloxy)-1,3-butadienes with 5-aryl- and 5-vinyl-3-acyl-4,5- dihydrofurans: Efficient synthesis of 5-(4-chlorobut-2-en-1-yl)- and 5-(2-aryl-2-chloroethyl)salicylates
Lau, Matthias,Sher, Muhammad,Villinger, Alexander,Fischer, Christine,Langer, Peter
scheme or table, p. 3743 - 3753 (2010/09/03)
The domino "[3+3] cyclization-ring-opening" reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-acetyl-5vinyl-4, 5-dihydrofurans afforded 5-(4-halobut-2-en-1-yl)salicylates. The reactions of 1,3-bis(trimethylsilyloxy)-1,3butadienes with 3-acetyl
Alkylation of β-dicarbonyl compounds as a method for the production of functionally substituted dihydrofurans
Maharramov,Sadikhova,Mammadov,Allahverdiyev
experimental part, p. 400 - 404 (2010/02/28)
The alkylation of some representatives of β-dicarbonyl compounds by 1,4-dibromo-2-butene and ethyl 2,3-dibromopropionate was investigated.
Nickel-catalyzed borylative ring-opening reaction of vinylcyclopropanes with bis(pinacolato)diboron yielding allylic boronates
Sumida, Yuto,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 4677 - 4679 (2009/05/26)
(Chemical Equation Presented) Vinylcyclopropanes bearing one or two electron-withdrawing groups on the cyclopropane ring undergo nickel-catalyzed borylative ring opening with bis(pinacolato)diboron to yield allylic boronates. The reaction proceeded with h
Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans
Bowman, Roy K.,Johnson, Jeffrey S.
, p. 573 - 576 (2007/10/03)
Mild Ni(0)-catalyzed rearrangements of 1-acyl-2-vinylcyclopropanes have been developed. The room-temperature isomerizations afford dihydrofuran products in yields regularly greater than 90%. A highly substituted, stereochemically defined cyclopropane was
Cyclodehydration of cis-2-butene-1,4-diol with active methylene compounds catalyzed by a diphosphinidenecyclobutene-coordinated palladium complex
Murakami, Hiromi,Matsui, Yukio,Ozawa, Fumiyuki,Yoshifuji, Masaaki
, p. 3151 - 3156 (2007/10/03)
(π-Allyl)palladium triflate coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB-OMe), [Pd(η3-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes cyclodehydration of cis-2-butene-
