Catalytic Asymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines

Liu, Xihong; Wang, Yijie; Yang, Dongxu; Zhang, Jinlong; Li, Dongsheng; Wu, Songhua

doi:10.1002/anie.201602880

Cited by 63 publications

(12 citation statements)

References 74 publications

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“…This is of particular importance, because such asymmetric reactions would allow for the preparation of analogues of Eli-Lilly’s γ-lactam antibiotics. On the other hand, the majority of catalytic asymmetric [3+2] cycloadditions of azomethine imines to alkenes have been performed using various organocatalysts, although examples of transition-metal-catalyzed reactions have also been reported [ 11 , 37 , 38 , 57 ]. The use of other dipolarophiles, such as cumulenes, imines, thiones, and nitriles, is another unexplored field of asymmetric cycloadditions of azomethine imines.…”

Section: Discussionmentioning

confidence: 99%

“…In general, azlactones prepared from different amino acids were very well tolerated, as well as azlactones containing diverse (hetero)aryl substituents in the C2-position. Azomethine imines with different substituents on the aromatic ring and various substituents at the 4-position of the phenyl ring of the arylsulfonyl protecting group were very well compatible with the developed protocol ( Scheme 34 ) [ 57 ].…”

Section: Synthesis Of Pyrazolidinesmentioning

confidence: 99%

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Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

et al. 2017

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Asymmetric [3+2] cycloadditions of azomethine imines comprise a useful synthetic tool for the construction of pyrazole derivatives with a variable degree of saturation and up to three stereogenic centers. As analogues of pyrrolidines and imidazolidines that are abundant among natural products, pyrazoline and pyrazolidine derivatives represent attractive synthetic targets due to their extensive applications in the chemical and medicinal industries. Following the increased understanding of the mechanistic aspect of metal-catalyzed and organocatalyzed [3+2] cycloadditions of 1,3-dipoles gained over recent years, significant strides have been taken to design and develop new protocols that proceed efficiently under mild synthetic conditions and duly benefit from superior functional group tolerance and selectivity. In this review, we represent the current state of the art in this field and detailed methods for the synthesis of non-racemic pyrazolines and pyrazolidines via [3+2] metal and organocatalyzed transformations reported since the seminal work of Kobayashi et al. and Fu et al. in 2002 and 2003 up to the end of year 2017.

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Section: Discussionmentioning

confidence: 99%

Section: Synthesis Of Pyrazolidinesmentioning

confidence: 99%

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

et al. 2017

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“…In 2016, Su, Liu, and co-workers reported that the chiral thiourea catalyzed double-activation mode was applied to promote the asymmetric IED cycloadditions of azomethine imines with azlactones (Scheme 17). 46 As azlactones [47][48][49][50] contain multiple reactive sites enabling either [3+3] or [3+2] cycloadditions, two kinds of conceivable cycloaddition product structure were proposed. After careful study followed by optimization, it was shown that the [3+2] cycloadducts, enantioenriched C 1 -substituted pyrazolidinefused THIQs 39 were obtained in high yields and with good to excellent diastereo-and enantioselectivities using bifunctional organocatalyst C13.…”

Section: Ied [3+2] Cycloaddition Of Cn-cyclic N′-acyl Azomethine Iminesmentioning

confidence: 99%

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

Chen

Gao

2020

Synthesis

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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

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“…In the case of reaction with imines, excellent progress has been made with Mannich reactions (C4)– or 1,3‐dipolar cycloaddition (C4 and C2),, but [2+2] cyclizations (C4 and C5) have been extremely limited. Motivated by the previous work on [2+3] cyclization with azomethine imines and our interest in azlactones,, we wondered whether the right choice of imine and catalyst could ensure that azlactones undergo [2+2] cyclization with imines to give α‐amino‐β‐lactams.…”

Section: Figurementioning

confidence: 99%

Phosphoric Acid Catalyzed Asymmetric [2+2] Cyclization/Penicillin–Penillonic Acid Rearrangement

Zhang

Xie

et al. 2018

Angewandte Chemie

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Enantioselective synthesis of imidazolidin‐5‐ones through a phosphoric acid catalyzed reaction between azlactones and N‐substituted β‐carbolines is reported. The reaction takes place via an initial formal [2+2] cycloaddition to generate an α‐amino‐β‐lactam, which subsequently undergoes an acid‐catalyzed asymmetric penicillin–penillonic acid (PPA) rearrangement with high diastereo‐ and enantioselectivity. To the best of our knowledge, this represents the first [2+2] cyclization of azlactones with imines and the first asymmetric PPA rearrangement, which are linked together by the phosphoric acid catalyst.

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Catalytic Asymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines

Cited by 63 publications

References 74 publications

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

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

Phosphoric Acid Catalyzed Asymmetric [2+2] Cyclization/Penicillin–Penillonic Acid Rearrangement

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