Rhodium-Catalyzed [3 + 2] Annulation of Cyclic <i>N</i>-Acyl Ketimines with Activated Olefins: Anticancer Activity of Spiroisoindolinones

Sharma, Satyasheel; Oh, Yongguk; Mishra, Neeraj Kumar; De, Umasankar; Jo, Hyeim; Sachan, Richa; Kim, Hyung Sik; Jung, Young Hoon; Kim, In Su

doi:10.1021/acs.joc.6b02708

Cited by 100 publications

(42 citation statements)

References 58 publications

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“…In 2017, Kim's group reported a rhodium(III)‐catalyzed [3+2] annulation of N ‐acyl ketimine derivatives with maleimides . This method leads to the formation of spiroisoindolinone derivatives in good to excellent yields in a highly stereoselective manner.…”

Section: Annulation Of Aromatics With Maleimidesmentioning

confidence: 99%

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

2019

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Maleimide and succinimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines and γ-lactams. A transition-metal-catalyzed chelationassisted functionalization of inert CÀ H bond of organic molecules with electrophiles or nucleophiles is one of the efficient methods to construct chemical bonds in a highly atom-and step-economical manner. The present review describes the recent advances in the reaction involving maleimides with organic molecules by a chelation-assisted inert CÀ H bond activation methodology. The reaction involving maleimides with organic molecules having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N-sulfonyl ketimine, carboxylic acids, and aldimines, were described. The scope, limitation and mechanistic investigation of the alkylation, annulation and alkenylation reactions were discussed elaborately. This review article includes the entire report on the chemical bondforming reaction of maleimides with organic molecules by the CÀ H bond activation strategy until the end of 2018.

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Section: Annulation Of Aromatics With Maleimidesmentioning

confidence: 99%

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

2019

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“…Cyclic imines are of prime importance as they could lead to the formation of spirocompounds via a [3 + 2] annulation reaction. In 2016, Kim described The Rh(III)-catalyzed redox-neutral coupling process of N-acyl ketimines generated in situ from 3-hydroxyisoindolinones with a wide range of activated olefins (Scheme 48) [147]. This approach led to the synthesis of bioactive spiroisoindolinone derivatives in good yields.…”

Section: Construction Of Spiroheterocyclesmentioning

confidence: 99%

Rh(III)-Catalyzed C–H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers

et al. 2019

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Rh(III)-catalyzed C–H activation features mild reaction conditions, good functional group tolerance, high reaction efficiency, and regioselectivity. Recently, it has attracted tremendous attention and has been employed to synthesize various heterocycles, such as indoles, isoquinolines, isoquinolones, pyrroles, pyridines, and polyheterocycles, which are important privileged structures in biological molecules, natural products, and agrochemicals. In this short review, we attempt to present an overview of recent advances in Rh(III)-mediated C–H bond activation to generate diverse heterocyclic scaffolds with sp3 carbon centers.

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“…(3)]. [117] It was found that olefins of maleimides, maleates, fumarates, and cinnamates led to the formation of spiroindane products via the [3+ +2] annulation, while acrylates and quinones furnished unsaturated spiroindene products resulting from b-H elimination ands ubsequent Prins-typecyclization.…”

Section: With Cyclic Aryl Ketiminesmentioning

confidence: 99%

“…Very recently, a rhodium‐catalyzed [3+2] annulation of N ‐acyl ketimines with various activated olefins is described by the Kim group [Eq. (3)] . It was found that olefins of maleimides, maleates, fumarates, and cinnamates led to the formation of spiroindane products via the [3+2] annulation, while acrylates and quinones furnished unsaturated spiroindene products resulting from β‐H elimination and subsequent Prins‐type cyclization.…”

Section: N‐substituted Quaternary Centersmentioning

confidence: 99%

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

2018

Chemistry A European J

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Efficient construction of quaternary carbon centers represents one of the most challenging goals in organic synthesis, and it has drawn tremendous research interest from organic chemist community. The past decade has witnessed a significant advancement of direct C-H functionalization, which delivers various synthetic tools for assembling structurally diversified architectures with the advantage of step- and atom-economy, operational simplicity, and readily available substrates. In this Minireview, synthetic methods based on transition-metal-catalyzed C-H functionalization as efficient tools for the construction of quaternary carbon centers are summarized.

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Rhodium-Catalyzed [3 + 2] Annulation of Cyclic N-Acyl Ketimines with Activated Olefins: Anticancer Activity of Spiroisoindolinones

Cited by 100 publications

References 58 publications

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

Rh(III)-Catalyzed C–H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

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