121642-09-9Relevant articles and documents
CuCl/air-mediated oxidative coupling reaction of imidazoheterocycles with N -aryl glycine esters
Jiao, Jing,Zhang, Jun-Rong,Liao, Yan-Yan,Xu, Li,Hu, Maolin,Tang, Ri-Yuan
, p. 30152 - 30159 (2017)
A copper/air mediated oxidative coupling reaction of imidazoheterocycles with N-aryl glycine esters is here described. The reaction proceeded effectively under an air atmosphere without the use of peroxide agents. This simple protocol allows for the preparation of a wide range of imidazoheterocycles with a glycine ester motif, which are of great interest in the field of medicinal chemistry. Interestingly, the coupling of imidazo[1,2-a]pyridine with secondary or tertiary α-amino phenylethanone selectively affords the imidazo[1,2-a]pyridin-3-yl imine or imidazo[1,2-a]pyridin-3-yl diketone in the presence of CuCl and TBHP (tertbutyl hydroperoxide).
Tin powder-promoted oxidation/allylation of glycine esters: Synthesis of γ,δ-unsaturated α-amino acid esters
Zhao, Pengfei,Huang, Danfeng,Wang, Feng,Han, Tongyu,Yang, Ming,Wang, Ke-Hu,Hu, Yulai
, (2021/10/20)
An efficient tin powder-promoted oxidation/allylation reaction of glycine esters with allyl bromides is developed, which affords γ,δ-unsaturated α-amino acid esters under mild conditions without any other transition metal catalysts. This method avoids the use of unstable imine as starting material, and provides an efficient method for synthesis of γ,δ-unsaturated α-amino acid esters and α-methylene-γ-lactam derivatives. Additional supporting information may be found in the online version of this article at the publisher's web site.
Unlocking the direct photocatalytic difluoromethylation of CN bonds
Alemán, José,Garrido-Castro, Alberto F.,Gini, Andrea,Maestro, M. Carmen
supporting information, p. 3769 - 3772 (2020/04/10)
The current study presents a direct CF2H radical addition to CN bonds predicated on the photocatalytic activation of commercially available zinc difluoromethanesulfinate. The mild conditions in place lead to impressive structural diversity, as quinoxalinones and dibenzazepines, among others, are successfully functionalized.
Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids
Ji, Peng,Zhang, Yueteng,Wei, Yongyi,Huang, He,Hu, Wenbo,Mariano, Patrick A.,Wang, Wei
supporting information, p. 3086 - 3092 (2019/05/01)
An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.
Polarity-Reversed Addition of Enol Ethers to Imines under Visible Light: Redox-Neutral Access to Azide-Containing Amino Acids
Yang, Sen,Zhu, Shuangyu,Lu, Dengfu,Gong, Yuefa
supporting information, p. 8464 - 8468 (2019/10/14)
A three-component and polarity-reversed addition cascade with a glyoxylate-based imine, an enol ether, and TMSN3 was established for the construction of γ-azido amino acids under visible light. This transformation features mild and redox-neutra
Asymmetric Organocatalytic Synthesis of Bisindoles – Scope and Derivatizations
Retich, Christina,Br?se, Stefan
supporting information, p. 60 - 77 (2018/01/17)
Starting from 3-vinylindoles and glyoxolate imines, we created a library of diverse 4,6-bis(1H-indole-3-yl)piperidine 2-carboxylates by using 10 mol-% of a chiral phosphoric acid. Utilising electron-withdrawing groups on the starting material during the r
Copper-Catalyzed Addition of Alkylboranes to Iminoacetates: Access to α-Alkyl Branched α-Amino Acids
Xiao, Xinsheng,Zhang, Wei,Lu, Xiaoxia,Deng, Yuanfu,Jiang, Huangfeng,Zeng, Wei
, p. 2497 - 2509 (2016/08/16)
A copper(I)-catalyzed addition of alkylborane reagents to α-iminoacetates has been developed to assemble both acyclic and cyclic α-branched α-amino carboxylic acid derivatives in good yields. A wide variety of unactivated alkenes are well tolerated in this transformation. (Figure presented.).
Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals
Fava, Eleonora,Millet, Anthony,Nakajima, Masaki,Loescher, Sebastian,Rueping, Magnus
supporting information, p. 6776 - 6779 (2016/06/09)
Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.
Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels-Alder Reaction of Arynes and KF-Induced Annulation
Reddy, R. Santhosh,Lagishetti, Chandraiah,Chen, Shuo,Kiran, I. N. Chaithanya,He, Yun
supporting information, p. 4546 - 4549 (2016/09/28)
The transition-metal-free multicomponent coupling of arynes, anilines, and ethylglyoxylate, proceeding via an inverse electron-demand aza Diels-Alder cycloaddition and N-arylation, has been demonstrated. This protocol allows rapid access to N-aryl dihydrophenanthridine derivatives in moderate to high yields at room temperature from readily available starting materials. In addition, an unprecedented fluoride induced annulation of ethyl(arylimino)acetates led to the formation of highly functionalized oxoimidazolidine derivatives in good yields under mild conditions.
Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine- 2 carboxylates
Zhong, Sabilla,Nieger, Martin,Bihlmeier, Angela,Shi, Min,Braese, Stefan
supporting information, p. 3265 - 3270 (2014/05/06)
We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-