865714-07-4Relevant academic research and scientific papers
Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates
Liu, Teng,He, Chixian,Wang, Fan,Shen, Xiang,Li, Yongqin,Lang, Man,Li, Guijun,Huang, Chao,Cheng, Feixiang
, p. 518 - 526 (2020/10/12)
A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.
Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates
Liu, Honglei,Jia, Hao,Wang, Bo,Xiao, Yumei,Guo, Hongchao
supporting information, p. 4714 - 4717 (2017/09/23)
The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.
Phosphine-Catalyzed Enantioselective [4 + 3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles
Yuan, Chunhao,Zhou, Leijie,Xia, Miaoren,Sun, Zhanhu,Wang, Dongqi,Guo, Hongchao
supporting information, p. 5644 - 5647 (2016/11/17)
With the use of a commercially available chiral phosphine as the catalyst, the first catalytic enantioselective [4 + 3] annulation of allenoates with C,N-cyclic azomethine imines is developed. The reaction works efficiently under mild reaction conditions to afford seven-membered ring-fused quinazoline-based tricyclic heterocycles in high yields with good to excellent diastereo- and enantioselectivities.
Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes
Wurz, Ryan P.,Fu, Gregory C.
, p. 12234 - 12235 (2007/10/03)
Although tertiary phosphines have emerged as remarkably versatile nucleophilic catalysts, there has been only very limited progress in achieving asymmetric catalysis with chiral phosphines. In this report, the first highly enantioselective variant of the
An application of the phosphine-catalyzed [4 + 2] annulation in indole alkaloid synthesis: Formal syntheses of (±)-alstonerine and (±)-macroline
Tran, Yang S.,Kwon, Ohyun
, p. 4289 - 4291 (2007/10/03)
(Chemical Equation Presented) An application of the phosphine-catalyzed [4 + 2] annulation in the formal synthesis of alstonerine and macroline is reported. A phosphine-catalyzed [4 + 2] reaction between imine 7a and allene 8 formed the D ring of the targ
