35207-75-1Relevant academic research and scientific papers
Synthesis of bicyclic tetrahydrofurans from linear precursors using manganese(III) acetate
Chany, Anne-Caroline,Marx, Léo B.,Burton, Jonathan W.
, p. 9190 - 9193 (2015)
We have recently developed methodology based on oxidative radical reactions for the synthesis of [3.3.0]-bicyclic lactones containing both cyclopentanes and γ-lactams along with application of this methodology to the synthesis of natural products and complex molecular architectures. Herein we report an extension of this methodology to the synthesis of oxygen heterocycles including bicyclic bis-lactones.
Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion
Jha, Neha,Singh, Roushan Prakash,Saxena, Paridhi,Kapur, Manmohan
supporting information, p. 8694 - 8698 (2021/11/24)
An Ir(III)-catalyzed C(3)-H alkylation of N-acetyl-1,2-dihydroisoquinolines with diverse acceptor-acceptor diazo compounds has been achieved under a single catalytic system via metal carbene migratory insertion. Moreover, further synthetic transformations of the alkylated products such as aromatization, selective decarboxylation, and decarbonylation lead to the formation of several synthetically viable isoquinoline derivatives having immense potentials.
Rhodium-Catalyzed [4+2] Annulation of N-Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone-Fused Cinnolines
Lin, Chih-Yu,Huang, Wan-Wen,Huang, Ying-Ti,Dhole, Sandip,Sun, Chung-Ming
supporting information, p. 4984 - 4992 (2021/09/28)
An efficient synthesis of novel dinitrogen-fused heterocycles such as pyrazolo[1,2-a]cinnoline derivatives have been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with α-diazo compounds. This reaction proceeds through a cascade C?H activation/intramolecular cyclization with a broad substrate scope. Furthermore, this protocol is successfully extended to the unusual phosphorus-containing α-diazo compounds and cyclic diazo compounds as the cross-coupling partners to deliver the two new kinds of pyrazolo[1,2-a]cinnolinones. The control experiments were performed to reveal insight into the mechanism of this reaction, involving reversible C?H activation, migratory insertion of the diazo compound, and cascade cyclization as the key steps of the transformation. Moreover, gram-scale synthesis and further transformation of the target product demonstrate the synthetic utility of the present protocol.
Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes
Xu, Xi,Dong, Shunxi,Feng, Lili,Wang, Sijing,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2692 - 2696 (2020/03/30)
An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.
Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
Ariafard, Alireza,Babaahmadi, Rasool,Dasgupta, Ayan,Gierlichs, Lukas,Melen, Rebecca L.,Stefkova, Katarína
supporting information, p. 15492 - 15496 (2020/07/20)
Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.
Strain Release of Donor-Acceptor Cyclopropyl Boronate Complexes
Gregson, Charlotte H. U.,Ganesh, Venkataraman,Aggarwal, Varinder K.
supporting information, p. 3412 - 3416 (2019/05/10)
The reactivity of boronate complexes which resemble donor-acceptor cyclopropanes is described. The enantioenriched cyclopropyl boronate complexes were shown to undergo concerted 1,2-metalate rearrangement/ring opening upon activation with a Lewis acid. Th
Asymmetric synthesis of novel spirocycles via a chiral phosphoric acid catalyzed desymmetrization
Kelley, Amber M.,Minerali, Eni,Wilent, Jennifer E.,Chambers, Nicholas J.,Stingley, Kyla J.,Wilson, G. Tyler,Petersen, Kimberly S.
supporting information, p. 1262 - 1264 (2019/04/10)
A straightforward method for the asymmetric preparation of novel lactone and lactam spirocycles is described. An initial desymmetrization via a chiral Br?nsted acid yields enantioenriched lactones which readily undergo a second cyclization to give the des
Catalyst-Controlled Chemodivergent Annulation to Indolo/Pyrrolo-Fused Diazepine and Quinoxaline
Dhole, Sandip,Chiu, Wei-Jung,Sun, Chung-Ming
supporting information, p. 2916 - 2925 (2019/04/26)
Catalyst-controlled chemodivergent annulation between o-indolo anilines and diazo compounds has explored for the synthesis of indolo-fused diazepine and quinoxaline. Under the Rh(III) catalyst, reaction proceeded through the free amine assisted C2?H activation followed by amidation leading to the diazepino[1,7-a]indole in a highly selective manner. While with Ru(II) catalyst, reaction involves formation Ru?carbene complex followed by ?NH2 group insertion and cascade cyclization via metallo-ene type reaction, β-hydride elimination to furnish the indolo[1,2-a]quinoxaline as the predominating product. This strategy directs modular approach towards the construction of unique indolo-fused diazepine/quinoxaline as well as pyrrolo-fused diazepine/quinoxaline scaffolds in excellent yields. (Figure presented.).
Regioselective oxidative ring-opening of cyclopropenyl carboxylates by visible light photoredox catalysis
Ye, Qianwen,Ye, Hongqiang,Cheng, Dongping,Li, Xiaonian,Xu, Xiaoliang
supporting information, p. 2546 - 2549 (2018/05/28)
Catalyzed by Ir(dFCF3ppy)2(dtbbpy)PF6, several aroyl methylidenemalonates were synthesized in good to excellent yields via visible light photoredox-catalyzed the oxidative ring-opening of cyclopropenyl carboxylate derivatives. The possible mechanism of oxidative quenching cycle was proposed.
Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone
Biswas, Aniruddha,Samanta, Rajarshi
, p. 1426 - 1436 (2018/04/06)
A straightforward RhIII-catalyzed strategy was developed for the site-selective C4-alkylation and C2-annulation of indole by using electronically variable diazo esters. The transformation was accomplished with the assist of an oxime directing group at the C3 position of the indole core with wide scope and functional-group tolerance. The method directly provided an indolopyridone core. The selectivity was triggered by the reactivity of the diazo coupling partner.
