Generation of Functionalized Azepinone Derivatives via a (4 + 3)-Cycloaddition of Vinyl Ketenes and α-Imino Carbenes Derived from <i>N</i>-Sulfonyl-triazoles

Hill, Harrison; Tucker, Zachary D.; Rodriguez, Kevin X.; Wendt, Katelyn A; Ashfeld, Brandon L.

doi:10.1021/acs.joc.1c03002

Cited by 4 publications

(3 citation statements)

References 45 publications

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“…Shen and Xu successfully demon-Scheme 5. [3 + n] cycloadditions of sulfonyltriazole with heterocyclics [43][44][45][46][47][48][49][50][51][52][53][54].…”

Section: [3 + N] Cycloadditions Of Sulfonyltriazole With Heterocyclesmentioning

confidence: 99%

“…Specifically, cyclopropane 37 underwent ring opening to afford compound 38. The Ashfeld group reported an alternative approach to C-C bond cleavage within the ring [47]. They developed an intermolecular rhodium(II) catalyzed formal [4 + 3] cycloaddition reaction between vinyl ketenes 39 and triazoles.…”

Section: [3 + N] Cycloadditions Of Sulfonyltriazole With Heterocyclesmentioning

confidence: 99%

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Skeletal Editing: Ring Insertion for Direct Access to Heterocycles

Li,

2024

Molecules

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Skeleton editing has rapidly advanced as a synthetic methodology in recent years, significantly streamlining the synthesis process and gaining widespread acceptance in drug synthesis and development. This field encompasses diverse ring reactions, many of which exhibit immense potential in skeleton editing, facilitating the generation of novel ring skeletons. Notably, reactions that involve the cleavage of two distinct rings followed by the reformation of new rings through ring insertion play a pivotal role in the construction of novel ring skeletons. This article aims to compile and systematize this category of reactions, emphasizing the two primary reaction types and offering a thorough exploration of their associated complexities and challenges. Our endeavor is to furnish readers with comprehensive reaction strategies, igniting research interest and injecting fresh impetus into the advancement of this domain.

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“…Shen and Xu successfully demon-Scheme 5. [3 + n] cycloadditions of sulfonyltriazole with heterocyclics [43][44][45][46][47][48][49][50][51][52][53][54].…”

Section: [3 + N] Cycloadditions Of Sulfonyltriazole With Heterocyclesmentioning

confidence: 99%

Section: [3 + N] Cycloadditions Of Sulfonyltriazole With Heterocyclesmentioning

confidence: 99%

Skeletal Editing: Ring Insertion for Direct Access to Heterocycles

Li,

2024

Molecules

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“…[48] The optimal conditions for this reaction were Very recently, Ashfeld's group developed a methodology for the preparation of azepinone derivatives 122 from vinyl ketenes 125 and N-sulfonyl-1,2,3-triazoles 120 (Scheme 32). [49] Various 1,4-dipolar surrogates are available for this intermolecular rhodium mediated (4 + 3)-cycloaddition, howbeit vinyl ketenes enriched favorable yield. After testing numerous catalysts, it was found that Rh 2 (Oct) 4 was most effective in dispensing the considered product azepinone 122.…”

Section: Rhodium-catalyzed Approachesmentioning

confidence: 99%

Metal‐Catalyzed Approaches for the Construction of Azepinones

et al. 2022

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The azepinone scaffolds are an important framework of pharmaceutically interesting compounds and many bioactive natural products. This review mainly focused on the metalcatalyzed approaches towards the synthesis of azepinones . Mainly it covers cycloisomerization and metal carbenoid insertion. It also involves transformations through cycloaddition reactions, metathesis reactions, microwave reactions and direct CÀ H/CÀ C/CÀ N activation reactions. The applications, substrate scope, limitations and plausible mechanisms of these transformations have also been discussed.

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(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Nicolai

Waser

2022

Angewandte Chemie

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Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) annulative addition of aryl and amino donoracceptor cyclopropanes with 2-aza-1,3-dienes. Densely substituted azepane derivatives were obtained in good to excellent yields and with high diastereoselectivity. The reaction occurred under mild conditions with ytterbium triflate as the catalyst. The use of copper triflate with a trisoxazoline (Tox) ligand led to an enantioselective transformation. The obtained cycloadducts were convenient substrates for a series of further modifications, showing the synthetic utility of these compounds.

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Generation of Functionalized Azepinone Derivatives via a (4 + 3)-Cycloaddition of Vinyl Ketenes and α-Imino Carbenes Derived from N-Sulfonyl-triazoles

Cited by 4 publications

References 45 publications

Skeletal Editing: Ring Insertion for Direct Access to Heterocycles

Skeletal Editing: Ring Insertion for Direct Access to Heterocycles

Metal‐Catalyzed Approaches for the Construction of Azepinones

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

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