37614-58-7Relevant academic research and scientific papers
Bi(OTf)3-catalyed One-pot Synthesis of α-Halo-β-amino Ketones and Acyl Aziridines from 3-Aryl Propargyl Alcohols
Zhang, Qinglin,Duan, Yongbin,Guo, Huifeng,Yang, Hong,Zhai, Jiulong,Li, Tiantian,Wang, Zhihai,Lu, Xiaolei,Wang, Yan,Yin, Yan
supporting information, p. 1832 - 1838 (2021/06/09)
A Bi(OTf)3-catalyed reaction of 3-aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated, which provided a facile route for the synthesis of a large variety of α-halo-β-amino ketones. The key intermediates, β-amino
Organocatalytic Regio- and Enantioselective N-Alkylation of Isoxazol-5-ones
Li, Pengfei,Liu, Meiwen,Qian, Chenxiao
supporting information, p. 6777 - 6780 (2021/12/31)
A chiral phosphoric acid catalyzed regio- and enantioselective reaction between 1-acylamino-3-arylprop-2-yn-1-ols and isoxazol-5-ones has been developed for the first time. With the established protocol, N-alkylation of isoxazol-5-ones was achieved, affording enantioenriched N,N-acetals in 74–99 % yield with 72–88 % ee.
Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
Chen, Xiaojuan,Fu, Liping,Huo, Xiaoli,Shao, Jiaan,Yu, Liya,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian
supporting information, p. 16430 - 16433 (2021/10/01)
A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
One-pot synthesis of 3-substituted-4H-[1,2,3] triazolo[5,1-c][1,4]oxazin-6(7H)-ones from propargyl alcohols, chloroacetyl chloride, and sodium azide
Chen, Jun-Min,Liu, Xiao-Ling,Sheng, Shou-Ri,Wei, Mei-Hong,Zhang, Xiao-Lan
, p. 482 - 485 (2020/11/30)
An efficient, one-pot synthesis of 3-substituted-4H-[1,2,3]triazolo[5,1-c][1,4]oxazin-6(7H)-ones is developed via sequential esterification, substitution, and 1,3-dipolar cycloaddition processes of various propargyl alcohols, chloroacetyl chloride, and so
When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions
Laher, Romain,Marin, Christophe,Michelet, Véronique
supporting information, p. 4058 - 4062 (2020/04/20)
An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the association of IPrAuCl with NaBArF. The remarkable selectivity was demonstrated on a 1 g and 25 g scale with low catalyst loadings. The synthetic utility of these low-molecular-weight enols was further demonstrated by the derivatization of some adducts and by the unprecedented olfactory evaluation of all bicyclic derivatives.
Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes
Dykstra, Ryan,Gutierrez, Osvaldo,Martin, Robert T.,Tambar, Uttam K.,Troian-Gautier, Ludovic,Xu, Bin
supporting information, p. 6206 - 6215 (2020/04/27)
Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.
Bi(OTf)3 catalyzed synthesis of acyclic β-sulfanyl ketones via a tandem Meyer-Schuster rearrangement/conjugate addition reaction
Wang, Yuan,Yin, Yan,Zhang, Qinglin,Pan, Wanyong,Guo, Huifeng,Pei, Keke
supporting information, p. 2030 - 2034 (2019/07/03)
A new strategy to prepare acyclic β-carbonyl thioethers from propargyl alcohols and sulfur nucleophiles is reported. The investigation of the reaction substrates scope indicated that primary 3-aryl propargyl alcohols and thiols underwent the transformation smoothly. The reaction probably proceeded a Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement of 3-aryl propargyl alcohol, followed by a thiol Michael conjugate addition of thiols to in situ generated α, β-unsaturated ketones. The method was 100% atom economic, high-yielding, and easy to handle, making it a valuable method for the construction of β-carbonyl sulfides.
Gold(i)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-: B] indole and indolo[2,3-a] quinolizine derivatives
Liu, Chengjun,Sun, Zenghui,Xie, Fukai,Liang, Guoduan,Yang, Lu,Li, Yaqiao,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
supporting information, p. 14418 - 14421 (2019/12/05)
Experimental and theoretical explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-
Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
Da Silva, Vitor A. F.,Da Silva, Gustavo P.,Matsuo, Bianca T.,Ali, Akbar,Davis, Rebecca L.,Zukerman-Schpector, Julio,Corrêa, Arlene G.,Paix?o, Márcio W.
supporting information, p. 519 - 526 (2019/01/24)
A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.
Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization
Zhou, Bingnan,Wu, Qiuyue,Dong, Ziyang,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 3594 - 3599 (2019/05/24)
A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.
