A chiral cobalt(<scp>ii</scp>) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction

Shen, Bin; He, Qianwen; Dong, Shujuan; Liu, Xiaohua; Feng, Xiaoming

doi:10.1039/d0sc00542h

Cited by 28 publications

(12 citation statements)

References 77 publications

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“…Only imine could be formed in the reaction of cinnamyl alcohol with aniline ( 3o ). 4-Chloro-N-(2-furylmethyl) aniline ( 3v ) and 4-bromine-N-(2-furylmethyl) aniline ( 3w ) were also obtained with high yields by this protocol, both of which were crucial intermediates for the synthesis of pharmaceuticals [ 66 , 67 , 68 ].…”

Section: Resultsmentioning

confidence: 99%

N, S Co-Coordinated Zinc Single-Atom Catalysts for N-Alkylation of Aromatic Amines with Alcohols: The Role of S-Doping in the Reaction

Zhang

Reng

et al. 2023

Nanomaterials

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S-doping emerged as a promising approach to further improve the catalytic performance of carbon-based materials for organic synthesis. Herein, a facile and gram-scale strategy was developed using zeolitic imidazole frameworks (ZIFs) as a precursor for the fabrication of the ZIF-derived N, S co-doped carbon-supported zinc single-atom catalyst (CNS@Zn1-AA) via the pyrolysis of S-doped ZIF-8, which was modified by aniline, ammonia and thiourea and prepared by one-pot ball milling at room temperature. This catalyst, in which Zn is dispersed as the single atom, displays superior activity in N-alkylation via the hydrogen-borrowing strategy (120 °C, turnover frequency (TOF) up to 8.4 h−1). S-doping significantly enhanced the catalytic activity of CNS@Zn1-AA, as it increased the specific surface area and defects of this material and simultaneously increased the electron density of Zn sites in this catalyst. Furthermore, this catalyst had excellent stability and recyclability, and no obvious loss in activity after eight runs.

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Section: Resultsmentioning

confidence: 99%

N, S Co-Coordinated Zinc Single-Atom Catalysts for N-Alkylation of Aromatic Amines with Alcohols: The Role of S-Doping in the Reaction

Zhang

Reng

et al. 2023

Nanomaterials

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“…Encouraged by the racemic example reported by Baskaran, Feng and Liu (2020) disclosed the first chiral Co(II) complex-catalyzed enantioselective cascade aza-Piancatelli rearrangement/Diels-Alder reaction of 2-furylcarbinols with N-(furan-2-ylmethyl)anilines employing their privileged chiral N,N′-dioxide ligands (Scheme 24). 54 This powerful process allows for efficient construction of diverse hexahydro-2a,5-epoxycyclopenta[cd]isoindoles bearing six contiguous stereocenters with excellent enantio-and diastereoselectivities.…”

Section: Enantioselective Cascade Aza-piancatelli Rearrangement/diels-alder Reactionmentioning

confidence: 99%

Recent Advances on Piancatelli Reactions and Related Cascade Processes

Zhong¹,

Xu²,

Cai³

2021

Synthesis

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The Piancatelli reaction, which is the rearrangement of 2-furylcarbinol to cyclopentenone, involves a key furanoxonium ion intermediate and a furan ring opening-4π electrocyclization process. In recent years, the original oxa-Piancatelli reaction has been extended to a large family of aza- and carbo-Piancatelli reactions and related cascade processes, providing a powerful platform for the construction of diverse functionalized cyclopentenones and polycyclic cyclopentanones. Meanwhile, chiral Brønsted/Lewis acid based catalytic asymmetric approaches to Piancatelli reactions have also been achieved for the assembly of highly valued chiral cyclopentenone scaffolds. In this short review, we present an overview of the recent developments in these areas and focus primarily on reports published in the last five years.1 Introduction2 Diastereoselective Oxa-, Aza- and Carbo-Piancatelli Reactions3 Diastereoselective Cascade Piancatelli Reactions4 Asymmetric Piancatelli Reactions and Related Cascade Processes5 Miscellaneous Furanoxonium Ion-Based Rearrangements6 Conclusion

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“…The cobalt-catalyzed synthesis of hexahydro-2a,5epoxycyclopenta[cd]isoindoles with six contiguous stereocenters starting with 2-furylcarbinols and N-(furan-2-ylmethyl)anilines has been developed by Feng, Liu, and others. [10] The combination of Co(BF 4 ) 2 with chiral N,N'-dioxide ligand 5 gave products in low to excellent yields with excellent enantio-and diastereoselectivities (Scheme 5). The cascade transformation includes the aza-Piancatelli rearrangement and Diels-Alder reaction.…”

Section: Cobalt-catalyzed Processesmentioning

confidence: 99%

Stereoselective Synthesis of Azacycles Induced by Group 8–11 Late Transition Metals

Molnár

2021

Eur J Org Chem

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The aim of the present minireview is to summarize and discuss recent advances in the field of stereoselective synthesis of azacycles. The focus is on studies that appeared in the last two years to illustrate recent trends with a handful of examples from 2019 highlighting an important field of enantioselective chemistry. Results collected and discussed here show that syntheses catalyzed by late transition metals of group 8-11 afford products in high yield with high stereoselectivity, often under mild reaction conditions thereby demonstrating their efficacy to afford valuable products. Plausible reaction mechanisms for most transformations are also discussed.

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A chiral cobalt(ii) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction

Abstract: An asymmetric aza-Piancatelli rearrangement/Diels–Alder cascade reaction between 2-furylcarbinols and N-(furan-2-ylmethyl)anilines was realized by using a chiral N,N′-dioxide/cobalt(ii) complex catalyst.

Cited by 28 publications

References 77 publications

N, S Co-Coordinated Zinc Single-Atom Catalysts for N-Alkylation of Aromatic Amines with Alcohols: The Role of S-Doping in the Reaction

N, S Co-Coordinated Zinc Single-Atom Catalysts for N-Alkylation of Aromatic Amines with Alcohols: The Role of S-Doping in the Reaction

Recent Advances on Piancatelli Reactions and Related Cascade Processes

Stereoselective Synthesis of Azacycles Induced by Group 8–11 Late Transition Metals

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