868659-08-9Relevant academic research and scientific papers
Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones
Cui, Hao,Duan, Zheng,Li, Er-Qing,Li, Ke,Mathey, Fran?ois,Song, Manman,Wang, Congcong,Wang, Yue,Wei, Donghui
, p. 3740 - 3746 (2020)
A copper-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described. By usingde novodesign of P-stereogenic phosphines as ligands, spiro[pyrrolidin-3,3'-oxindole]s are generated in good to excellent yields with high asymmetric induction. A further reduced catalyst loading of 0.1 mol% is sufficient to achieve a satisfactory enantioselectivity of 90% ee. The DFT calculations suggest the second Michael addition of the 1,3-dipole to be the rate- andenantio-determining step. A key feature of this 1,3-dipolar cycloaddition is the wide substrate applicability, even with alkyl aldehyde-derived azomethine ylide; thus it has streamlined a highly enantioselective access to a new class of antiproliferative agents, MDM2-p53.
Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo?-methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles
Gan, Zhenjie,Li, Ke,Zhang, Hui,Li, Er-Qing
supporting information, p. 1331 - 1340 (2020/11/30)
A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo?-addition?-of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- A nd enantioselectivity, broad substrate scope and mild reaction conditions.
Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines
Zhi, Mengna,Gan, Zhenjie,Ma, Rong,Cui, Hao,Li, Er-Qing,Duan, Zheng,Mathey, Fran?ois
supporting information, (2019/05/07)
A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo-(up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled predominantly by the P-stereogenic phosphines.
Enantiodivergent Combination of Natural Product Scaffolds Enabled by Catalytic Enantioselective Cycloaddition
Xu, Hao,Golz, Christopher,Strohmann, Carsten,Antonchick, Andrey P.,Waldmann, Herbert
supporting information, p. 7761 - 7765 (2016/07/07)
An efficient strategy has been established for the enantiodivergent synthesis of natural product inspired compounds embodying both tropane and pyrrolidine natural product fragments. This strategy includes the enantioselective kinetic resolution of racemic tropanes by means of a copper(I)-catalyzed [3+2] cycloaddition and allows the preparation of two enantiopure products in a one-pot reaction in high yield and with high diastereo- and enantioselectivity by using one chiral catalyst.
Asymmetric [3+2] cycloaddition of azomethine ylides catalyzed by silver(I) triflate with a chiral bipyrrolidine-derived phosphine ligand
Gu, Xin,Xu, Zhen-Jiang,Che, Chi-Ming,Lo, Vanessa Kar-Yan
, p. 3307 - 3314,8 (2012/12/12)
Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The AgOTf + L1 protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%).
Asymmetric [3+2] cycloaddition of azomethine ylides catalyzed by silver(I) triflate with a chiral bipyrrolidine-derived phosphine ligand
Gu, Xin,Xu, Zhen-Jiang,Lo, Vanessa Kar-Yan,Che, Chi-Ming
, p. 3307 - 3314 (2013/01/15)
Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The AgOTf + L1 protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%). Georg Thieme Verlag Stuttgart.New York.
Sc(OTf)3-catalyzed tandem [3+2] cycloaddition/nucleophilic ring-opening reaction of cyclopropane 1,1-diesters with azomethine ylides
Fang,Hu,Ren,Wang
experimental part, p. 1479 - 1487 (2011/12/22)
A new Sc(OTf)3-catalyzed tandem reaction combined with a dimerized self-[3+2] cycloaddition of azomethine ylide and a nucleophilic ring-opening of cyclopropane 1,1-diester has been developed. A series of polyfunctionalized imidazolidine derivatives were synthesized by this reaction (Yield 44-77 %). In some cases, this tandem reaction was also accompanied by a cross-[3+2] cycloaddition of cyclopropane 1,1-diester with imine.
