Formal [5+3] Cycloaddition of Vinylethylene Carbonates with Isatin‐Based α‐(Trifluoromethyl)imines for Diastereoselective Synthesis of Medium‐Heterocycle‐Fused Spirooxindoles

Zhao, Hong‐Wu; Wang, Li‐Ru; Jia, Guo; Ding, Wan-Qiu; Song, Xiaoyan; Wu, Huihui; Tang, Zhe; Fan, Xiao‐Zu; Bi, Xiao-Fan

doi:10.1002/adsc.201900651

Cited by 36 publications

(6 citation statements)

References 36 publications

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“…(5 + 3) cyclization is one of the most effective methods to construct eight-membered heterocycles [ 102 , 103 , 104 , 105 , 106 , 107 ]. However, it is challenging to conduct the asymmetric version of the reaction, and this problem needs to be addressed.…”

Section: Nitrogen-based Pyridinium and Quinolinium 14-zwitterionsmentioning

confidence: 99%

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

et al. 2023

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Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles and have received increasing attention in recent years. In particular, pyridinium and quinolinium 1,4-zwitterions have been widely studied and used in a variety of cyclization reactions due to their air stability, ease of use, and high efficiency. Sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions, types of emerging heteroatom-containing synthons, have attracted much attention from chemists. These 1,4-zwitterions, which contain multiple reaction sites, have been successfully used in the synthesis of three- to eight-membered cyclic compounds over the last decade. In this review, we present the exciting progress made in the field of cyclization reactions of sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions. Moreover, the mechanistic insights, the transition states, some synthetic applications, and the challenges and opportunities are also discussed. We hope to provide an overview for synthetic chemists who are interested in the heterocycle synthesis from cyclization reaction with pyridinium and quinolinium 1,4-zwitterions pyridinium and quinolinium 1,4-zwitterions.

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Section: Nitrogen-based Pyridinium and Quinolinium 14-zwitterionsmentioning

confidence: 99%

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

et al. 2023

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“…Subsequently, Zhao and co-workers also presented a diastereoselective [3 + 5] cycloaddition reaction of N -2,2,2-trifluoroethylisatin ketimines 1 with VECs 119 [ 65 ]. Differently from before, the reaction was carried out under the catalyst system of Pd(PPh 3 ) 4 , PPh 3 , and pyridine.…”

Section: Organocatalytic Reactions Involving N -22...mentioning

confidence: 99%

Recent Advances of N-2,2,2-Trifluoroethylisatin Ketimines in Organic Synthesis

Liu

Wang

et al. 2023

Molecules

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The special properties of fluorine atoms and fluorine-containing groups have led to an increasing number of applications for fluorine-containing organic compounds, which are also extremely widely used in the field of new drug development. Unfortunately, naturally fluorinated organics are rare in nature, so the selective introduction of fluorine atoms or fluorine-containing groups into organic molecules is very important for pharmaceutical/synthetic chemists. N-2,2,2-trifluoroethylisatin ketimines have received the attention of many chemists since they were first developed as fluorine-containing synthons in 2015. This paper reviews the organic synthesis reactions in which trifluoroethyl isatin ketimine has been involved in recent years, focusing on the types of reactions and the stereoselectivity of products, and also provides a prospect of its application in this field.

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“…Analogous decarboxylative [5+3] cycloadditions of VECs 8 with N ‐2,2,2‐Trifluoroethylisatin ketimines 57 was also disclosed almost at same time by Shi an Zhao independently (Scheme 34). [22] In Zhao's work, the reactions were conducted in reflux 1,2‐dichloroethane (DCE) by using Pd(PPh 3 ) 4 as catalyst, PPh 3 as ligand and pyridine as additive, affording the eight‐membered heterocycle fused spirooxindoles 59 in one step with good yields and excellent diastereoselectivities [22a] . However, acids including Lewis and Brønsted acid as additive failed to give the target products.…”

Section: π‐Allyl Palladium Bearing O‐nucleophilementioning

confidence: 99%

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

You

Zhang

et al. 2022

ChemCatChem

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Palladium‐catalyzed decarboxylative cycloadditions have emerged as highly effective methods for constructing structurally diverse carbo‐ and heterocycles because of the formation of at least two carbon‐carbon or carbon‐heteroatom bonds in a single step. It is of great interest to chemists that this type of cycloaddition reactions possesses some special advantages such as high reactivity, exclusive regioselectivity, and good functional group compatibility. Based on these qualities, palladium‐catalyzed decarboxylative cycloadditions present strong ability in synthetic chemistry and have been flourished especially in the last five years. In this review, the achievements in palladium‐catalyzed decarboxylative cycloadditions involving cyclic carbonates, carbamates, and lactones for accessing oxacyclo‐, azacyclo‐ and carbocyclic compounds are addressed. Mechanistic insights and some synthetic applications toward the synthesis of natural products are discussed. The challenges and opportunities of this field are also outlined.

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Formal [5+3] Cycloaddition of Vinylethylene Carbonates with Isatin‐Based α‐(Trifluoromethyl)imines for Diastereoselective Synthesis of Medium‐Heterocycle‐Fused Spirooxindoles

Cited by 36 publications

References 36 publications

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

Recent Advances of N-2,2,2-Trifluoroethylisatin Ketimines in Organic Synthesis

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

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