Formal [5+3] Cycloaddition between Isatin-Based α-(Trifluoromethyl)imine Ylides and Vinyloxiranes: Diastereoselective Access to Medium-Heterocycle-Fused Spirooxindoles

Zhao, Hong‐Wu; Wang, Liru; Ding, Wan-Qiu; Jia, Guo; Tang, Zhe; Song, Xiaoyan; Wu, Huihui; Fan, Xiao‐Zu; Bi, Xiao-Fan; Zhong, Qi‐Di

doi:10.1055/s-0040-1706537

Cited by 9 publications

(8 citation statements)

References 2 publications

(1 reference statement)

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“…A similar diastereoselective [3 + 5] cycloaddition reaction of trifluoroethylisatin ketimines 1 with vinyloxiranes 127 was established by the Zhou group in 2021 ( Scheme 46 ) [ 66 ]. In the presence of Pd 2 (dba) 3 ·CHCl 3 , PPh 3, and 60% NaH, this reaction enables the synthesis of medium-heterocycle-fused spirooxindole compounds with excellent diastereoselectivities (all >20:1 dr) in moderate to good yields (52–87%).…”

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

confidence: 96%

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

confidence: 96%

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

Liu

Wang

et al. 2023

Molecules

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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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“…33 Previously, N -2,2,2-trifluoroethylisatin ketimines 58 were utilized as 1,3-dipoles in the presence of a base and underwent [3 + n ] cycloadditions with electron-deficient dipolarophiles or catalytically generated zwitterionic dipoles, typically generating achiral cycloadducts. 34 In this work, an asymmetric oxa-[4 + 3] cycloaddition was achieved using a Pd catalyst and chiral ligand L23 in the absence of a base. In fact, not adding a Lewis base was the key to achieving high enantioselectivity and diastereoselectivity of the desired products 59 .…”

Section: Oxa-[4 + 3] Dipolar Cycloadditionsmentioning

confidence: 99%