Dearomatization Reactions of Electron‐Deficient Aromatic Rings

Tsukano, Chihiro; Takemoto, Yoshiji

doi:10.1002/9783527698479.ch11

Cited by 7 publications

(6 citation statements)

References 113 publications

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“…Representative examples of transition-metal-catalyzed CADA reactions via allylic and propargylic substitution and related reactions, cross-coupling reactions, oxidation, amination, and halogenation reactions are presented. On the other hand, CADA reactions via carbenoid-mediated reactions, 6 hydrogenation reactions, 7 cycloaddition reactions, 8 Reissert-type reactions, 9 and diverse applications of CADA reactions in the total synthesis of natural products 10 are not covered. In addition, we provide readers with clear clues on how the discussed CADA reactions evolved to their current form.…”

Section: The Bigger Picturementioning

confidence: 99%

Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds

Zheng

You

2016

Chem

496

105

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Catalytic asymmetric dearomatization (CADA) reactions refer to those reactions converting aromatic compounds into enantio-enriched three-dimensional cyclic molecules in a catalytic fashion. In the past, this area has seen significant progress since a series of valuable strategies for asymmetric catalysis were successfully applied. In this review, we provide insightful discussions on recent representative examples of asymmetric dearomatization reactions catalyzed by transition-metal complexes. Close attention is paid to the mechanism, scope, limitations, and the future direction of CADA reactions.

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Section: The Bigger Picturementioning

confidence: 99%

Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds

Zheng

You

2016

Chem

496

105

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“…The asymmetric nucleophilic addition to electron-deficient (hetero)aromatic compounds constitutes another important category of dearomatization reactions, with the Reissert reaction being the most famous example. 7 In this section, we highlight some recent contributions on the catalytic asymmetric dearomative cyclization reactions of 3-nitroindoles initiated by nucleophilic additions at the C2 position of the indole ring.…”

Section: Arenes As Electrophilesmentioning

confidence: 99%

“…Historically, Birch reduction, Buchner ring-expansion, and the Reimer–Tiemann reaction of para-substituted phenols were among the rare examples of named reactions for dearomatization (Scheme c), which were usually operated under harsh conditions or with narrow substrate scopes. Notably, the nucleophilic addition and hydrogenation reactions of aromatic compounds can be promoted by chiral catalysts. Besides, enzyme-catalyzed transformations are well-known for dearomatization reactions, which are exemplified by the arene cis-dihydroxylation promoted by arene dioxygenase enzymes …”

Section: Introductionmentioning

confidence: 99%

Advances in Catalytic Asymmetric Dearomatization

2021

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Asymmetric catalysis has been recognized as the most enabling strategy for accessing chiral molecules in enantioenriched forms. Catalytic asymmetric dearomatization is an emerging and dynamic research subject in asymmetric catalysis, which has received considerable attention in recent years. The direct transformations from readily available aromatic feedstocks to structurally diverse three-dimensional polycyclic molecules make catalytic asymmetric dearomatization reactions of broad interest for both organic synthesis and medicinal chemistry. However, the inherent difficulty for the disruption of aromaticity demands a large energy input during the dearomatization process, which might be incompatible with the conditions generally required by asymmetric catalysis. In this Outlook, we will discuss representative strategies and examples of catalytic asymmetric dearomatization reactions of various aromatic compounds and try to convince readers that by overcoming the above obstacles, catalytic asymmetric dearomatization reactions could advance chemical sciences in many respects.

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“…3 However, vinylogous Mukaiyama reactions under anion-binding organocatalysis 4 has long been prevented, most probably as a consequence of the longrange enantioinduction that the silyl dienolate would require. 5 Inspired by the power of dearomatisation methods 6 and the anion-binding catalysed asymmetric functionalisation of activated N-heteroarenes such as (iso)quinolines and pyridines by nucleophilic addition, 4,7,8 we tackled this deficiency in the vinylogous-Mukaiyama technology. To the best of our knowledge, the use of silyl dienol ether derivatives as vinylogous nucleophiles in this type of asymmetric dearomatisation process has never been accomplished.…”

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confidence: 99%