Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel–Crafts reactions with a chiral bifunctional heterogeneous catalyst

Cheng, Hong‐Gang; Miguélez, Javier; Miyamura, Hiroyuki; Yoo, Woo‐Jin; Kobayashi, Shū

doi:10.1039/c6sc03849b

Cited by 20 publications

(11 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was found that this heterogeneous catalyst was capable of facilitating the sequential aerobic oxidation-asymmetric Pictet-Spengler reaction between benzyl alcohols 128 and Naminoethylpyrroles 120. [87] The combined catalytic system of PI/CB-Au/Pd and (S)-TRIP promoted the tandem sequence rendering piperazines 129 in excellent yield and enantioselectivity when benzyl alcohols 128 bearing eletron-donating substituents were employed. For electron withdrawing substituents, a modification in the catalytic system was necessary with the new composite material PI/CB-Au/Pt in order to achieve good ee's (Scheme 58).…”

Section: Brønsted Acid Catalyzed Pictet-spengler-type Reactionsmentioning

confidence: 99%

“…Kobayashi and coworkers developed a new class of chiral bifunctional heterogeneous materials XLV composed of Au/Pd nanoparticles and chiral phosphoric acids as active orthogonal catalysts. It was found that this heterogeneous catalyst was capable of facilitating the sequential aerobic oxidation‐asymmetric Pictet‐Spengler reaction between benzyl alcohols 128 and N ‐aminoethylpyrroles 120 [87] . The combined catalytic system of PI/CB–Au/Pd and ( S )‐TRIP promoted the tandem sequence rendering piperazines 129 in excellent yield and enantioselectivity when benzyl alcohols 128 bearing eletron‐donating substituents were employed.…”

Section: Organocatalytic Fca Reactions Of Pyrrolesmentioning

confidence: 99%

See 1 more Smart Citation

Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

et al. 2021

View full text Add to dashboard Cite

Substituted and annulated pyrroles containing chiral centers are potentially accessible by means of an organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. They are interesting compounds because of their abundant natural occurrence and their different biological activities. In comparison to indoles, for which a myriad of asymmetric procedures involving the FCA have been developed, pyrroles have been relatively less used as nucleophilic counterparts in this reaction. However, in the last two decades, huge synthetic efforts have been performed around this interesting asymmetric transformation and several methodologies have been devised. In this context, this review article provides a general overview of the organocatalytic enantioselective FCA chemistry of pyrroles, which has not been revised to date. Reactions 2.4. Brønsted Acid Catalyzed Intramolecular FCA Reactions 3.Organocatalytic FCA Reactions with Dihydroindoles 4.Conclusions and Outlook

show abstract

Section: Brønsted Acid Catalyzed Pictet-spengler-type Reactionsmentioning

confidence: 99%

Section: Organocatalytic Fca Reactions Of Pyrrolesmentioning

confidence: 99%

Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[87] This one-pot sequence provided an efficient approach for the syn- Later, this method was used in integration of aerobic oxidation and intramolecular asymmetric addition reactions with a chiral bifunctional heterogeneous catalyst. [88]…”

Section: Binol-derived Phosphoric Acidsmentioning

confidence: 99%

Direct Asymmetric Arylation of Imines

et al. 2020

View full text Add to dashboard Cite

The Friedel-Crafts reaction represents one of the most efficient tools for the formation of carbon-carbon bonds and direct derivatization of aromatic compounds. Asymmetric arylation of imines involving Friedel-Crafts reaction has received much interest recently. The present review summarizes the works on the asymmetric arylation of imines by different approaches including Friedel-Crafts reaction and their development to date. The review is divided into three main sections: addition reaction of arenes to imines in the presence of chiral catalysts; addition reaction of arenes to imines containing chiral tails and asymmetric coupling reaction of aryl boronic acids and imines. 4.2. Palladium Catalysts with Chiral Ligands 4.3. Nickel Catalysts with Chiral Ligands 5. Conclusions

show abstract

“… 25 The catalytic resin admitted recycling in batch and the implementation of a flow process spanning 28 h. It is worth noting that, about the same time, Kobayashi et al reported on a very similar immobilisation strategy to obtain a hybrid material that combined supported TRIP and Au/Pd nanoparticles. 26 This heterogeneous catalyst exploited the benefits of both catalysts, allowing to carry out a sequence of oxidation and enantioselective aza -Friedel–Crafts reaction.…”

Section: Introductionmentioning

confidence: 99%

Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst

2018

View full text Add to dashboard Cite

show abstract

Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel–Crafts reactions with a chiral bifunctional heterogeneous catalyst

Abstract: A chiral heterogeneous material was prepared and evaluated as a bifunctional catalyst for the sequential aerobic oxidation-asymmetric intramolecular aza-Friedel–Crafts reaction.

Cited by 20 publications

References 60 publications

Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

Direct Asymmetric Arylation of Imines

Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst

Contact Info

Product

Resources

About