139575-14-7Relevant articles and documents
Dynamic Catalytic Highly Enantioselective 1,3-Dipolar Cycloadditions
Antonchick, Andrey P.,Brieger, Lukas,Grigalunas, Michael,Strohmann, Carsten,Waldmann, Herbert,Yildirim, Okan
supporting information, p. 20012 - 20020 (2021/08/06)
In dynamic covalent chemistry, reactions follow a thermodynamically controlled pathway through equilibria. Reversible covalent-bond formation and breaking in a dynamic process enables the interconversion of products formed under kinetic control to thermod
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
supporting information, p. 3740 - 3746 (2020/06/03)
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.
Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition
Liang, Lei,Niu, Hong-Ying,Wang, Dong-Chao,Yang, Xin-He,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 553 - 556 (2019/01/10)
Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.
