Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates

Wang, Yan; Wang, Qian; Zhu, Jieping

doi:10.1002/chem.201601548

Cited by 38 publications

(15 citation statements)

References 85 publications

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“…[40] In the presence of Cat. 8, various 3-hydroxymaleimides (27) and quinone monoamines (28) were involved in this [3 + 2]-annulation reaction, providing a broad range of novel succinimide-fused dihydrobenzofurans (29) with two continuous quaternary stereocenters in moderate to excellent yields (up to 99 %) with moderate to excellent enantioselectivities (up to 99 % ee) (Scheme 9). The authors proposed a plausible reaction mechanism based on the absolute configuration of one of the products.…”

Section: Stereoselective [3 + 2] Cycloadditionsmentioning

confidence: 99%

“…1,3‐Dipolar cycloadditions of azomethine imines with alkenes/alkynes play an impressive role in the construction of five‐membered heterocycles [6a] such as dihydropyrazoles or pyrazolidines, which are useful structural scaffolds found in natural products and bioactive compounds [26] . In this context, Zhu and co‐workers (2016) developed the chiral phosphoric acid‐catalyzed asymmetric inverse electron demand 1,3‐dipolar formal [3+2] cycloaddition of azomethine imines ( 1 ) with enecarbamates ( 2 or 3 ) [27] . In the presence of Cat.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

“…[26] In this context, Zhu and co-workers (2016) developed the chiral phosphoric acidcatalyzed asymmetric inverse electron demand 1,3-dipolar formal [3 + 2] cycloaddition of azomethine imines (1) with enecarbamates (2 or 3). [27] In the presence of Cat. 1 and Cat.…”

Section: Stereoselective 13-dipolar Cycloadditionmentioning

confidence: 99%

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Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances

2022

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Asymmetric cycloaddition/annulation reactions have contributed greatly to the synthesis of a variety of novel cyclic compounds used in organic synthesis, natural product synthesis, material science, and chemical biology. Thus, chiral phosphoric acid‐catalyzed asymmetric cycloaddition reactions have received the attention of the synthetic community to design new vital asymmetric reactions and synthesize complex molecules for the past two decades. Although several review articles on organocatalyzed asymmetric cycloaddition reactions can be found in the literature, there has been no specific review on CPA‐catalyzed asymmetric cycloaddition/annulation reactions. Herein, the most recent research progress on chiral phosphoric acid catalyzed asymmetric [3+2], [4+2], [2+2], [3+3], [4+3], [4+1] annulation, and 1,3‐dipolar cycloadditions have been compiled and analyzed to demonstrate the importance of chiral phosphoric acid catalysis in asymmetric cycloaddition or annulation reactions.

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Section: Stereoselective [3 + 2] Cycloadditionsmentioning

confidence: 99%

Section: Cycloaddition Reactionsmentioning

confidence: 99%

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Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances

2022

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“…Zhu reported the chiral SPA‐catalyzed asymmetric inverse electron demand 1,3‐dipolar cycloaddition of azomethine imines with ene‐carbamates (Scheme 36). [ 40 ] Chiral phosphoric acid catalyst ( S ) ‐ SPA 22 was capable of catalyzing the [3+2] cycloaddition model reaction to afford the desired product in excellent yield and diastereoselectivity (>19 : 1).…”

Section: Asymmetric Organocatalysismentioning

confidence: 99%

Chiral Spirocyclic Phosphoric Acids and Their Growing Applications

et al. 2021

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What is the most favorite and original chemistry developed in your research group? Developing SPINOL-phosphoric acids (SPAs), TM-SPINOL-phosphoric acids (SPAs 2.0) and PCP-derived planar chiral phosphoric acids (PPAs) for asymmetric catalysis. What is the most important personality for scientific research? Curiosity, optimism, self-confidence and persistence. What's your hobbies? What's your favorite book(s)? I enjoy cooking. My favorite book is Journey to the West. Who influences you mostly in your life? My mother. What is your favorite journal(s)? The journals publishing the original and systematic work of synthetic chemistry. Could you please give us some advices on improving Chinese Journal of Chemistry? Fast review, fast publication, fast promotion via new media.

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“…Again, different substitution patterns (substituents) on the aromatic ring of azomethine imines 110 were well tolerated, whereas increasing the size of the β-substituent of the ( Z )-enecarbamate resulted in deceleration of the reaction, which at room temperature led to decreased enantioselectivity. Finally, reaction with benzyl [( E )-prop-1-en-1-yl]carbamate afforded the corresponding product with significantly reduced stereoselectivity ( Scheme 35 ) [ 58 ].…”

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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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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Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates

Cited by 38 publications

References 85 publications

Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances

Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances

Chiral Spirocyclic Phosphoric Acids and Their Growing Applications

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

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