Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

Yang, Fang; Han, Tian-Jiao; Jia, Shi-Kun; Wang, Min‐Can; Mei, Guang‐Jian

doi:10.1039/d3cc00160a

Chem. Commun.

2023

DOI: 10.1039/d3cc00160a

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Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

Fang Yang

Tian-Jiao Han

Shi-Kun Jia

et al.

Abstract: The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes was established. Owing to the absence of carbenoid intermediate, this protocol represents the first non-carbenoid variant of Doyle−Kirmse reaction. Under...

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Cited by 8 publications

References 92 publications

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Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Li,

Ma,

Meng

et al. 2023

Adv Synth Catal

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Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made in the past years. Among them, organocatalysis, in particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient and reliable method for the preparation of diverse and valuable functionalized spirooxindoles. According to different kinds of nucleophilic catalysts, we summarize and classify three catalytic strategies; these are tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed cycloadditions, and tertiary phosphine‐catalyzed cycloadditions, respectively. Through these methods, potential bioactive spirooxindole skeletons owning various functional groups can be produced to enrich the small organic molecule library. In this review, we describe a comprehensive and updated advances of nucleophilic Lewis base catalytic cycloaddition reactions for the construction of spirooxindoles. Meanwhile, the related mechanism and the application of these annulation strategies in natural product total synthesis will be highlighted in detail.

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Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Li,

Ma,

Meng

et al. 2023

Adv Synth Catal

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Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides

Gao,

Miao,

Sun

et al. 2023

Advanced Science

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Herein, the first diversity‐oriented catalytic asymmetric dearomatization of indoles with o‐quinone diimides (o‐QDIs) is reported. The catalytic asymmetric dearomatization (CADA) of indoles is one of the research focuses in terms of the structural and biological importance of dearomatized indole derivatives. Although great achievements have been made in target‐oriented CADA reactions, diversity‐oriented CADA reactions are regarded as more challenging and remain elusive due to the lack of synthons featuring multiple reaction sites and the difficulty in precise control of chemo‐, regio‐, and enantio‐selectivity. In this work, o‐QDIs are employed as a versatile building block, enabling the chemo‐divergent dearomative arylation and [4 + 2] cycloaddition reactions of indoles. Under the catalysis of chiral phosphoric acid and mild conditions, various indolenines, furoindolines/pyrroloindolines, and six‐membered‐ring fused indolines are collectively prepared in good yields with excellent enantioselectivities. This diversity‐oriented synthesis protocol enriches the o‐quinone chemistry and offers new opportunities for CADA reactions.

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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Feng,

Xie,

Huang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAllenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties of organic compounds make allenes a desirable choice in various applications. Here, we report a facile method for the atom‐economical synthesis of propargyl allenylamines via an underdeveloped [2,3]‐sigmatropic rearrangement. Our strategy employs easily accessible propargylamines as starting materials, which are first converted into propargyl ammonium salts, followed by a base‐promoted [2,3]‐sigmatropic rearrangement. This one‐pot, two‐step reaction proceeds in the absence of transition metals, displays a very broad scope, and does not require the introduction of the electron‐withdrawing group into the starting materials.

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Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

Abstract: The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes was established. Owing to the absence of carbenoid intermediate, this protocol represents the first non-carbenoid variant of Doyle−Kirmse reaction. Under...

Cited by 8 publications

References 92 publications

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides

Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

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