Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3337-3355
Author(s):  
Dan Li ◽  
Wei Gao ◽  
Xiaochao Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Asymmetric Reactions ◽  
Structural Units ◽  
Mannich Reactions ◽  
Asymmetric Reaction ◽  
Azomethine Imines ◽  
Catalytic Asymmetric ◽  
Further Development ◽  
New Strategies

Tetrahydroisoquinoline (THIQ) scaffolds are important structural units that widely exist in a variety of natural alkaloids and synthetic analogues. Asymmetric synthesis of C1-chiral THIQ is of particular importance due to its significant pharmaceutical, agrochemical, and other biological activities, and the usually distinct bioactivities exhibited by the two enantiomers. In this review, we highlight the significant advances achieved in this field, present recent asymmetric synthesis with imines in isoquinoline rings ordered according to the sequence of various substrate types. New strategies could be inspired and more types of substrates need further development.1 Introduction2 Catalytic Asymmetric Reaction of Dihydroisoquinolines2.1 Asymmetric Reactions of 3,4-Dihydroisoquinolines2.2 Asymmetric Reactions of Dihydroisoquinolinium Salts2.3 Asymmetric Reactions of C,N-Cyclic N′-Acyl Azomethine Imines2.3.1 NED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.2 IED [3+2] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.3 [3+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.4 [4+3] Cycloaddition of C,N-Cyclic N′-Acyl Azomethine Imines2.3.5 Asymmetric Addition Reactions to C,N-Cyclic N′-Acyl Azomethine Imines2.4 Asymmetric Reactions of C,N-Cyclic Nitrones3 Catalytic Asymmetric Mannich Reactions of Isoquinolines4 Conclusions and Perspectives

Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone

2019 ◽  
Vol 55 (84) ◽  
pp. 12715-12718 ◽  
Author(s):  
Huijun Yuan ◽  
Yao Li ◽  
Hanhui Zhao ◽  
Zhihong Yang ◽  
Xin Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Pyrazole Derivatives ◽  
Asymmetric Reaction ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Axially Chiral ◽  
Enantioselective Reaction ◽  
Catalytic Asymmetric

The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68–99%) with excellent enantioselectivities (83–98% ee) by utilizing chiral phosphoric acid as a catalyst.

Enantioselective construction of a 2,2′-bisindolylmethane scaffold via catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles

2015 ◽  
Vol 13 (29) ◽  
pp. 7993-8000 ◽  
Author(s):  
Yu-Xin Gong ◽  
Qiong Wu ◽  
Hong-Hao Zhang ◽  
Qiu-Ning Zhu ◽  
Feng Shi
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Asymmetric Reaction ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

A chiral phosphoric acid-catalyzed asymmetric reaction of 2-indolylmethanols with 3-alkylindoles has been established to construct 2,2′-bisindolylmethane scaffold in good enantioselectivities.

scholarly journals Untethering sparteine: 1,3-diamine ligand for asymmetric synthesis in water

2021 ◽  
Author(s):  
Fanyun Zeng ◽  
Chen Chen ◽  
Liu Liu ◽  
Yifan Li ◽  
Bo Li ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Cinchona Alkaloids ◽  
Phosphine Ligands ◽  
Asymmetric Induction ◽  
Asymmetric Reaction ◽  
Asymmetric Transformations ◽  
Chiral Diamine ◽  
Amine Ligands ◽  
Further Development ◽  
Reaction In Water

Chiral ligands are the toolbox for asymmetric synthesis to access 3D molecular world. Enabling efficient asymmetric reaction in water is a big challenge. As moisture/air stable and strong binding moieties, amines, compared to imine and phosphine ligands, are ideal candidates to accommodate asymmetric transformations in water. Known amine ligands like Proline analogues and Cinchona alkaloids showed excellent asymmetric induction. Sparteine, an alkaloid studied originated in 1968, had never been considered as a privileged catalyst due to its structure defection which led to poor reaction compatibility and unsatisfactory stereoselectivity. Here, we report the design of a chiral diamine catalyst untethering one of the sparteine rings. The diamine catalyst was easily accessed in two steps on 100 gram-scale. This chiral ligand was proved to be efficient for addition reactions in water providing products with excellent yields and enantiomeric ratios. This pluripotent catalyst has also shown good reactivity/enantioselectivity under organocatalysis, Cu and Pd-catalysed conditions. We anticipate that the ligand would allow further development of other catalysts for important yet challenging green stereoselective transformations.

scholarly journals Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

2016 ◽  
Vol 12 ◽  
pp. 1000-1039 ◽  
Author(s):  
Bin Yu ◽  
Hui Xing ◽  
De-Quan Yu ◽  
Hong-Min Liu
Keyword(s):  
Clinical Trials ◽  
Natural Products ◽  
Drug Discovery ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

Oxindole scaffolds are prevalent in natural products and have been recognized as privileged substructures in new drug discovery. Several oxindole-containing compounds have advanced into clinical trials for the treatment of different diseases. Among these compounds, enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3-substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations.

Recent advances in the catalytic asymmetric reactions of thiazolone derivatives

2020 ◽  
Vol 18 (31) ◽  
pp. 6018-6041
Author(s):  
Yong-Xing Song ◽  
Da-Ming Du
Keyword(s):  
Cascade Reactions ◽  
Asymmetric Reactions ◽  
Mannich Reactions ◽  
Michael Additions ◽  
Recent Advances ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

This review highlights the recent advances in catalytic asymmetric reactions of thiazolone derivatives, including Michael additions, Mannich reactions as well as various cascade reactions.

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