Chiral Brønsted acid-catalyzed conjugate addition of indoles to azadienes: Enantioselective synthesis of hetero-triarylmethanes

Xie, Haichao; Wu, Bo; Wang, Xinwei; Zhou, Yong‐Gui

doi:10.1016/s1872-2067(19)63396-6

Cited by 23 publications

(7 citation statements)

References 57 publications

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“…Zhou et al employed aurone-derived azadienes 214 as electrophilic coupling partners in the F−C reaction with indoles 215 to produce optically pure heterotriarylmethanes 216. 89 The CPAcatalyzed reaction tolerated very well the electron-donating or electron-withdrawing groups in the indole substrate, generating the corresponding heterotriarylmethanes in high yields (up to 95%) and good to high enantioselectivities (up to 98% ee; Scheme 44b). Based on the experimental results, a plausible transition-state model for the reaction was proposed.…”

Section: Reactions With Other Electrophilic Partnersmentioning

confidence: 99%

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

2022

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Functionalized chiral indole derivatives are privileged and versatile organic frameworks encountered in numerous pharmaceutically active agents and biologically active natural products. The catalytic asymmetric Friedel–Crafts reaction of indoles, catalyzed by chiral metal complexes or chiral organocatalysts, is one of the most powerful and atom-economical approaches to access optically active indole derivatives. Consequently, a wide range of electrophilic partners including α,β-unsaturated ketones, esters, amides, imines, β,γ-unsaturated α-keto- and α-ketiminoesters, ketimines, nitroalkenes, and many others have been successfully employed to achieve a plethora of functionalized chiral indole moieties. In particular, strategies for C–H functionalization in the phenyl of indoles require incorporation of a directing or blocking group in the phenyl or azole ring of indole. The discovery of chiral catalysts which can control enantiodiscrimination has gained a great deal of attention in recent years. This review will provide an updated account on the application of the asymmetric Friedel–Crafts reaction of indoles in the synthesis of diverse chiral indole derivatives, covering the timeframe from 2011 to today.

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Section: Reactions With Other Electrophilic Partnersmentioning

confidence: 99%

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

2022

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“…In 2019, Zhou's group reported a reaction between azadienes 41 and indoles 137 and obtained hetero-triarylmethane 138 via the chiral Brønsted acid-catalyzed Cat-30 (Scheme 22e). [99] Various hetero-triarymethanes with excellent enantioselectivities and broad substrate scope were obtained. In 2020, Shao's group developed the direct enantioselective Michael-type Friedel-Crafts arylations and heteroarylations of s-cis 1-azadienes as catalyzed by chiral bifunctional tertiary amine-urea catalysts or phosphoric acid catalysts (Scheme 22f).…”

Section: Addition Reactionmentioning

confidence: 99%

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Deng

Meng

2020

Chemistry An Asian Journal

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Benzothiophene, benzofuran, indole, and indene derivatives are privileged heterocyclic motifs. These are present in a wide range of bioactive natural products and pharmaceutical drugs and are the subject of materials science research. However, the construction of benzothiophene, benzofuran, indole, and indene frameworks have been long‐standing challenges to organic chemists. In this review, we classify the derivatives of four structures synthesized from 2‐benzylidene‐1‐benzofuran‐3‐one and their analogues in terms of their ring size (from three‐ to ten‐membered) and type (fused or spiro), as well as summarizing the developments of this field. Finally, we discuss the ring opening and 1,4‐addition reactions.

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“…Recently, BDAs have also been reported to act as 2-atom synthons in [2 + n ] cycloaddition reactions by several research groups for the synthesis of spiro-benzofurans (Scheme b) . In addition, the use of such species as a acceptor for 1,4-addition reactions has also been rapidly developed by using 1-naphthols, 5 H -thiazol-4-ones, phosphites, tritylthiols, unsaturated γ-lactones, indoles, and electron-rich alkenes as nucleophiles. However, to the best of our knowledge, all of the reported reactions involving BDAs reported so far are limited to cycloaddition and 1,4-addition reactions except for one example.…”

Section: Introductionmentioning

confidence: 99%

Substrate-Switched Chemodivergent Pyrazole and Pyrazoline Synthesis: [3 + 2] Cycloaddition/Ring-Opening Rearrangement Reaction of Azadienes with Nitrile Imines

et al. 2022

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By virtue of a fundamentally new reaction model of benzofuranderived azadienes (BDAs), an unprecedented synthesis of biologically important pyrazoles has been achieved through a tandem [3 + 2] cycloaddition/ring-opening rearrangement reaction of BDAs with nitrile imines. The nature and type of substrates are found to act as a chemical switch to trigger two distinct reaction pathways. A minor modification to the substrates allows the access to spiro-pyrazolines. Article pubs.acs.org/joc

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Chiral Brønsted acid-catalyzed conjugate addition of indoles to azadienes: Enantioselective synthesis of hetero-triarylmethanes

Cited by 23 publications

References 57 publications

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Substrate-Switched Chemodivergent Pyrazole and Pyrazoline Synthesis: [3 + 2] Cycloaddition/Ring-Opening Rearrangement Reaction of Azadienes with Nitrile Imines

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