42046-26-4Relevant academic research and scientific papers
Phosphine-Catalyzed Highly Enantioselective [3 + 3] Cycloaddition of Morita-Baylis-Hillman Carbonates with C,N-Cyclic Azomethine Imines
Zhang, Lei,Liu, Honglei,Qiao, Guanyu,Hou, Zhanfeng,Liu, Yang,Xiao, Yumei,Guo, Hongchao
, p. 4316 - 4319 (2015)
The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino[6,1-a]iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities and extremely excellent enantioselectivities (98->99% ee).
Asymmetric synthesis of tetrahydroisoquinoline derivatives through 1, 3-dipolar cycloaddition of C, N-cyclic azomethine imines with allyl alkyl ketones
Chen, Wenyan,Feng, Guipeng,Ma, Guoyang,Wang, Kaikai,Wang, Shaoyan,Xu, Shaohong
, (2021/06/17)
[3 + 2] A 1, 3-Dipolar cycloaddition of C, N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.
A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines
Zhang, Dan,Liu, Junwen,Kang, Zhenghui,Qiu, Huang,Hu, Wenhao
, p. 9844 - 9848 (2019/12/05)
A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.
Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition
Qurban, Saira,Du, Yu,Gong, Jun,Lin, Shao-Xia,Kang, Qiang
supporting information, p. 249 - 252 (2019/01/04)
An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.
Phosphane-Catalyzed [3+3] Annulation of C,N-Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen-Fused Heterocycles
Li, Zhen,Yu, Hao,Liu, Yang,Zhou, Leijie,Sun, Zhanhu,Guo, Hongchao
supporting information, p. 1880 - 1885 (2016/07/06)
A phosphane-catalyzed [3+3] annulation of azomethine imines with ynones has been developed. Under mild reaction conditions, the reaction proceeds smoothly to afford tricyclic dinitrogen-fused heterocyclic compounds in moderate to excellent yields with moderate to excellent stereoselectivies. Using a chiral phosphine as the catalyst, the reaction could work to give the cycloadduct in moderate yield with moderate enantioselectivity. (Figure presented.) .
Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates
Wang, Yang,Wang, Qian,Zhu, Jieping
supporting information, p. 8084 - 8088 (2016/06/14)
The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinoline-fused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields with excellent regio-, diastereo-, and enantioselectivities. The pyrazolidine ring can be opened to install an aminal, α-amino nitrile, or homoallylamine function with an excellent control of the newly generated stereogenic center. Access to aminobenzo[a]quinolizidine is also documented. Acid catalysis: The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinoline-fused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields with excellent regio-, diastereo-, and enantioselectivities (see scheme).
A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates
Wang, De,Lei, Yu,Wei, Yin,Shi, Min
, p. 15325 - 15329 (2016/02/18)
Catalytic asymmetric [3+2] cycloadditions of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild condition. The substrate scope has been also examined. This is the first time that δ-substituted allenoates have been applied as a δ,γ-C-C bond participated C 2 synthon in asymmetric synthesis. Another round: Catalytic asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild conditions. This is the first example applying δ-substituted allenoates as C 2 synthons in asymmetric δ,γ-C-C bond formation.
Stable azomethine imines having a 3,4-dihydroisoquinoline fragment and their cycloaddition to N-arylmaleimides
Koptelov,Saik,Molchanov
experimental part, p. 537 - 546 (2011/07/29)
Aroylation of 5,6,8,8a,13,14,16,16a-octahydro[1,2,4,5]tetrazino[6,1-a : 3,4-a']diisoquinoline or 1,3,4,8b-tetrahydro[1,2]diazireno[3,1-a]isoquinoline, as well as reactions of 2-(2-bromoethyl)benzaldehyde with aroylhydrazines followed by treatment with triethylamine, led to the formation of stable azomethine imines, aroyl(3,4-dihydroisoquinolinium-2-yl)azanides. 1,3-Dipolar cycloaddition of the latter to N-mesitylmaleimide was stereoselective: the ratio of the trans- and cis-adducts was (3-7) : 1, the former prevailing. The reactions with N-arylmaleimides having no ortho-substituents in the aryl group gave the corresponding cisadducts as the major products [trans/cis ratio 1 : (2.5-10)]. Pleiades Publishing, Ltd., 2011.
Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated aldehydes
Hashimoto, Takuya,Maeda, Yuko,Omote, Masato,Nakatsu, Hiroki,Maruoka, Keiji
supporting information; experimental part, p. 4076 - 4077 (2010/05/15)
(Figure Presented) A yet-unexploited class of azomethine imines, C,N-cyclic azomethine imines, could be successfully employed in highly enantioselective 1,3-dipolar cycloaddition with enals catalyzed by titanium-BINOLate to give pharmaceutically attractive tetrahydroisoquinoline and piperidine motifs. Copyright
