- Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes
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An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.
- Shen, Wen-Bo,Tang, Xiang-Ting,Zhang, Ting-Ting,Lv, Dong-Can,Zhao, Dan,Su, Tong-Fu,Meng, Lei
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- Tandem Reaction Approaches to Isoquinolones from 2-Vinylbenzaldehydes and Anilines via Imine Formation-6π-Electrocyclization-Aerobic Oxidation Sequence
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Two distinctive transition-metal-promoted aerobic oxidation protocols have been developed for the synthesis of isoquinolones from 2-vinylbenzaldehydes and aniline derivatives. Thus, the one-pot tandem reaction sequence of imine formation, thermal 6π-electrocyclization, followed by either Cu(OAc)2-mediated or Pd(OAc)2-catalyzed aerobic oxidation protocol allowed the ready access to isoquinolone derivatives. The control experiments revealed that the 1,2-dihydroisoquinoline intermediates from the 6π-electrocyclization of 1-azatrienes were aerobically oxidized to isoquinolones in the presence of either Cu(OAc)2 or Pd(OAc)2 catalyst.
- Lee, Jiyeon,Kim, Hun Young,Oh, Kyungsoo
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supporting information
p. 474 - 478
(2020/01/21)
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- Enantioselective Copper-Catalyzed Desymmetrization of 1,3-Diketones Involving Borylation of Styrenes
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A copper-catalyzed intramolecular enantioselective and diastereoselective borylative coupling of styrenes and ketones was achieved by merging desymmetrization strategy and olefin difunctionalization. The reaction proceeds through an initial enantioselective borylcupration of styrenes, followed by a highly selective direct addition to 1,3-diketones. The bicyclic scaffolds with three chiral carbon centers, including two tetrasubstituted carbons, were generated in excellent yields, diastereoselectivities, and enantioselectivities. This catalytic tandem reaction has great potential for further synthetic application of the chiral polycyclic compounds, because of the versatility of the functional groups in the products.
- Zheng, Purui,Han, Xiaoyu,Hu, Jiao,Zhao, Xiaoming,Xu, Tao
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supporting information
p. 6040 - 6044
(2019/08/27)
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- AgOTf-catalyzed sequential synthesis of 4-isoquinolones: Via oxidative ring opening of aziridines and aza-Michael addition
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An efficient AgOTf-catalyzed sequential reaction involving the oxidative ring-opening of aziridines by DMSO and aza-Michael addition has been developed. A series of 2,3-dihydro-4(1H)-isoquinolones were afforded in moderate to good yields by the formation of one new CO bond and one new C-N bond. The features of this sequential reaction include high bonding efficiency, use of a catalytic amount of catalysts, a broad substrate scope and mild conditions. This methodology provides a good choice for constructing the libraries of 2,3-dihydro-4(1H)-isoquinolones.
- Xing, Siyang,Cui, Hong,Gu, Nan,Li, Ying,Wang, Kui,Tian, Dawei,Qin, Jiajing,Liu, Qiaoyang
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supporting information
p. 8308 - 8312
(2017/10/23)
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- Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation
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A palladium-catalyzed aminopalladation reaction followed by nucleophilic addition with aldehydes and dehydration is described. This direct and operationally simple procedure provides a rapid and reliable approach to a wide range of functionalized tetrahydroisoquinolines with high selectivity. Mechanistic studies disclosed that the nucleophilic addition, performed via a highly ordered transition-state, is the turnover-limiting step in which the inherent β-hydride elimination of the key Csp3?Pd species was controlled by the confined conformation and the nucleophilicity of the Csp3?Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.
- Hu, Yue,Xie, Yinjun,Shen, Zhiqiang,Huang, Hanmin
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p. 2473 - 2477
(2017/02/23)
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- Photoredox-Catalyzed Three-Component Tandem Process: An Assembly of Complex Trifluoromethylated Phthalans and Isoindolines
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A novel photoredox-mediated tandem three-component process afforded a wide variety of CF3-containing phthalans and isoindolines in respectable yields and with moderate to excellent diastereoselectivity.
- Jarrige, Lucie,Carboni, Aude,Dagousset, Guillaume,Levitre, Guillaume,Magnier, Emmanuel,Masson, Géraldine
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supporting information
p. 2906 - 2909
(2016/07/06)
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- Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids
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Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.
- Calder, Ewen D. D.,McGonagle, Fiona I.,Harkiss, Alexander H.,McGonagle, Grant A.,Sutherland, Andrew
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p. 7633 - 7648
(2014/09/17)
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- Relay catalysis: Enantioselective synthesis of cyclic benzo-fused homoallylic alcohols by chiral bronsted acid-catalyzed allylboration/ring closing metathesis
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Six- and seven-membered benzo-fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral Bronsted acid-catalyzed allyl (crotyl)boration/ring closing metathesis sequence performed under orthogonal relay catalysis conditions. Excellent enantio- and diastereoselectivities are obtained in most of the cases. In addition, the parent crotylboration/RCM process is also described. The required substrates, ortho-vinylbenzaldehydes, are readily available in one step from commercially available starting materials. Both catalysts and reactants are also available from commercial suppliers. The reaction shows broad functional group compatibility and is also suitable for heteroaromatic substrates. Substitution at any position of the aromatic ring is tolerated; however, substitution at position 6 results in a substantial drop in enantioselectivity. Copyright
- Fustero, Santos,Rodriguez, Elsa,Lazaro, Ruben,Herrera, Lidia,Catalan, Silvia,Barrio, Pablo
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supporting information
p. 1058 - 1064
(2013/05/21)
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- Inter- and intramolecular hydroacylation of alkenes employing a bifunctional catalyst system
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Based on a conceptually innovative bifunctional P,N ligand, an efficient protocol for the rhodium-catalyzed inter- and intramolecular hydroacylation of alkenes has been developed.
- Vautravers, Nicolas R.,Regent, Damien D.,Breit, Bernhard
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supporting information; experimental part
p. 6635 - 6637
(2011/06/27)
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- A diversity-oriented synthesis of bicyclic cis -dihydroarenediols, cis -4-hydroxyscytalones, and bicyclic conduritol analogues
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A common-intermediate-based enantioselective strategy has been developed aiming at bicyclic arene cis-dihydrodiols, cis-4-hydroxyscytalones, and bicyclic mimics of conduritol. Key features of this protocol include Barrett's asymmetric hydroxyallylation, ring-closing metathesis (RCM), and completely regioselective Wacker oxidation of internal cyclic olefins.
- Mukherjee, Parag,Roy, Soumya J. Singha,Sarkar, Tarun K.
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supporting information; experimental part
p. 2472 - 2475
(2010/08/07)
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