203003-15-0Relevant academic research and scientific papers
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.
Application of the Cu(i)/TEMPO/O2 catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines
Luo, Zheng,Liu, Yan,Wang, Chao,Fang, Danjun,Zhou, Junyu,Hu, Huayou
supporting information, p. 4609 - 4613 (2019/09/09)
A Cu(i)/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)-catalyzed aerobic oxidative dehydrogenative aromatization reaction of fully saturated pyrrolidines to synthesize multi-substituted pyrroles was developed for the first time. The use of a non-precious metal catalyst, green oxidant and environmentally friendly solvent made the reaction more sustainable.
Enantioselective Mannich Reaction of Glycine Iminoesters with N-Phosphinoyl Imines: A Bifunctional Approach
Zhang, Changhui,Yang, Jiao,Zhou, Wenqiang,Tan, Qiuyuan,Yang, Zhao,He, Ling,Zhang, Min
supporting information, p. 8620 - 8624 (2019/11/03)
A bifunctional catalytic approach for the asymmetric Mannich reaction of glycine iminoesters with N-phosphinoyl imines has been developed. By the combination of metal catalysis and organocatalysis, the vicinal two stereogenic centers were efficiently constructed, affording a wide range of syn-diamino esters in high yields with excellent enantio- and diastereoselectivities (up to >99:1 dr, 99% ee).
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.
Metal-free asymmetric 1,3-dipolar cycloaddition of N-arylmaleimides to azomethine ylides catalyzed by chiral tertiary amine thiourea
Bai, Jian-Fei,Wang, Liang-Liang,Peng, Lin,Guo, Yun-Long,Ming, Jun-Nan,Wang, Fei-Ying,Xu, Xiao-Ying,Wang, Li-Xin
experimental part, p. 4472 - 4478 (2011/10/01)
The first metal-free asymmetric 1,3-dipolar cycloaddition of N-arylmaleimides to azomethine ylides catalyzed by chiral tertiary amine thiourea to form multiply substituted pyrrolidines in excellent yields (up to 89%) and enantioselectivities (up to 96% ee) is presented. This procedure allows a rapid diversity-oriented synthesis of chiral pyrrolidine derivatives with high optical purity. A series of bifunctional thiourea catalysts were applied for the first time to the highly asymmetric 1,3-dipolar cycloaddition of N-arylmaleimides to azomethine ylides togive the products in excellent yields (up to 89%) and enantioselectivities (up to 96% ee).
