Gold‐catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso‐Povarov Reactions

Chen, Ching‐Nung; Liu, Rai‐Shung

doi:10.1002/ange.201903615

Cited by 10 publications

(1 citation statement)

References 59 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A representative example is the Diels-Alder reaction served as a standard strategy to build six-membered rings, especially distinguished by forging all-carbon cyclohexenes [7][8][9][10][11] . Cycloaddition manipulation between N-aryl imines with dienophiles defined as the Povarov reaction, an extremely significant part of Diels-Alder reaction, has benefited the area of academy and industry because of the powerful capability of preparing widely utilized nitrogen-containing cycles [12][13][14][15][16][17][18][19] . Although numerous marvellous reactions have been discovered in this realm over the past decades, this type of cycloaddition appears only feasible to the C=C unsaturated systems (Scheme 1a), which somehow restricts the potency to create more contractually intriguing heterocycles [20][21][22] .…”

mentioning

confidence: 99%

In(OTf)3-Catalyzed Reorganization/Cycloaddition of Two Imine Units and Subsequently Modular Assembly of Acridinium Photocatalysts

Nan

Huang

Liu

et al. 2022

Preprint

View full text Add to dashboard Cite

Reorganization of unsaturated chemical bonds is one of the most promising strategies to generate architecturally diversified and innovative molecular library. Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)3 Lewis acid, which is sharply distinguished from the well-recognized [4+2] cycloaddition version with Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacridines have been synthesized with high functional group compatibility under concise reaction conditions. Preliminary mechanistic studies unravel that α，β-unsaturated imine likely serves as a pivotal intermediate. Notably, handing products give rise to a series of structurally novel and fine-tuneable acridinium photocatalysts, which offers a heuristic paradigm for synthesizing these ones and is also highlighted by facilitating several encouraging dihydrogen coupling reactions efficiently.

show abstract

mentioning

confidence: 99%

In(OTf)3-Catalyzed Reorganization/Cycloaddition of Two Imine Units and Subsequently Modular Assembly of Acridinium Photocatalysts

Nan

Huang

Liu

et al. 2022

Preprint

View full text Add to dashboard Cite

show abstract

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

et al. 2020

View full text Add to dashboard Cite

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode‐selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material‐tuned product selectivity.

show abstract

Gold‐Catalyzed [3+2]‐Annulations of α‐Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

et al. 2021

Self Cite

View full text Add to dashboard Cite

This work reports gold‐catalyzed [3+2]‐annulations of α‐diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3‐dihydrofurans with high regio‐ and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]‐annulations with α‐diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

show abstract

Gold‐catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso‐Povarov Reactions

Cited by 10 publications

References 59 publications

In(OTf)3-Catalyzed Reorganization/Cycloaddition of Two Imine Units and Subsequently Modular Assembly of Acridinium Photocatalysts

In(OTf)3-Catalyzed Reorganization/Cycloaddition of Two Imine Units and Subsequently Modular Assembly of Acridinium Photocatalysts

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

Gold‐Catalyzed [3+2]‐Annulations of α‐Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

Contact Info

Product

Resources

About