Diastereoselective construction of tetracyclic chromanes <i>via</i> a triply annulative strategy

Tang, Zhishun; Gao, Xiang; Yin, Pengxuan; Yang, Lü; Shi, Zhichuan; Zhao, Zhigang; Ye, Ling; Li, Xuefeng

doi:10.1039/d2ob00326k

Cited by 5 publications

(2 citation statements)

References 41 publications

(18 reference statements)

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“…Xu and co‐workers described thiourea 104 mediated organocatalytic Michael‐Michael cascade for the synthesis of 2,3,4‐trisubstituted chromanes 113 with excellent ee and de values (Scheme 23a) [42a] . Recently, Li and co‐workers devised a nitronate induced triple Michael‐aldol cascade on chalcones 114 bearing additional conjugation which led to structurally encumbered tetracyclic chromanes 115 with six chiral centers through formation of four new C−C bonds (Scheme 23b) [42b] . High diastereoselectivities observed in these reactions were attributed to an initial anti‐selective recursive nitronate cyclization to cyclohexanone intermediate 118 followed by a highly stereoselective intramolecular tandem Michael‐aldol cascade.…”

Section: Domino Synthesis Of Bi‐ and Tricyclic Ringsmentioning

confidence: 99%

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes as a source of recursive carbanions has created a niche operating space for generating molecular complexity and diversity. This new corollary i. e. recursive nitronate cyclization is the basis of a domino [5 C+1 C] cyclization strategy wherein nitroalkanes act as one‐carbon lynchpin, providing rapid access to topologically intriguing, densely functionalized carbo‐ and heterocycles embodying multiple chiral centers with regio‐, stereo‐ and enantioselectivity. Extension to aromatic domains, particularly via benzannulation reactions, has further consolidated the operating space. While leveraging the functional versatility of nitro group for post‐domino modifications, such endeavors have culminated in total synthesis of diverse natural products. An incisive analysis of recursive nitronate cyclizations and their emergent potentials is delineated in this review. It is hoped that this focused narrative will enthuse and draw new practitioners to the arena to advance the field.

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Section: Domino Synthesis Of Bi‐ and Tricyclic Ringsmentioning

confidence: 99%

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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“…However, there are no systematic review on enantioselective TM‐catalyzed synthetic approaches lead to five‐ and six‐ membered benzo O ‐heterocycles. Based on the continuing interests in enantioselective synthetic methodologies for heterocycles [22] as well as TM catalyzed reactions, [23] herein, we are aim to provide the first updated achievements in this specified topic. In this review the following topics are involved due to their widely studied: asymmetric hydrogenation, asymmetric allylic alkylation (AAA), Wacker‐type cyclization, alkene difunctionalization, asymmetric addition across carbonyl group, enantioselective annulation, asymmetric nucleophilic addition, concerted cycloaddition, catalytic C−H insertion, dearomative strategies, asymmetric C−H activation and intermolecular cross coupling reaction.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal‐Catalyzed Enantioselective Synthesis of Chiral Five‐ and Six‐Membered Benzo O‐heterocycles

Yang

Liang²,

Ding

et al. 2023

The Chemical Record

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Enantiomerically enriched five‐ and six‐membered benzo oxygen heterocycles are privileged architectures in functional organic molecules. Over the last several years, many effective methods have been established to access these compounds. However, comprehensive documents cover updated methodologies still in highly demand. In this review, recent transition metal catalyzed transformations lead to chiral five‐ and six‐membered benzo oxygen heterocycles are presented. The mechanism and chirality transfer or control processes are also discussed in details.

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Diastereoselective Synthesis of Bicyclo[3.2.1]octanes via Catalyst‐Free Cascade Michael/Henry Reaction with a Functionalized Vinylogous Nucleophile

Gao

Yang

et al. 2023

Adv Synth Catal

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A readily prepared and functionalized vinylogous nucleophile has been explored and utilized to construct bridged bicyclic compounds. The corresponding cascade Michael/Henry reaction occurred with relatively high reactivity under catalyst‐free and mild conditions. A range of structurally distinct bicyclo[3.2.1]octanes were generated in 40–96% isolated yields with excellent diastereoselectivities (≥10:1 dr). Gram‐scale synthesis was also demonstrated.

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Diastereoselective construction of tetracyclic chromanes via a triply annulative strategy

Abstract: A triple Michael/aldol cascade reaction has been established to construct tetracyclic chromanes in a diastereoselective fashion (≥5:1 dr). The polycyclic products were generated in 50-78% isolated yields under mild and...

Cited by 5 publications

References 41 publications

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

Transition Metal‐Catalyzed Enantioselective Synthesis of Chiral Five‐ and Six‐Membered Benzo O‐heterocycles

Diastereoselective Synthesis of Bicyclo[3.2.1]octanes via Catalyst‐Free Cascade Michael/Henry Reaction with a Functionalized Vinylogous Nucleophile

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