Rapid Construction of Polycyclic Skeletons via Brønsted-Base-Catalyzed Annulations of Ethylidene 1,3-Indenediones and Vinyl 1,2-Diketones DOI

Lixuan Zhu,

Haotian Luo,

Jinggong Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 5893 - 5898

Published: July 9, 2024

Brønsted-base-catalyzed diversified annulations between ethylidene 1,3-indenediones and vinyl 1,2-diketones have been achieved, delivering three types of products containing oxabicyclo[3.2.1]octane, spiro[4.5]decane, branched triquinane skeletons, respectively, which widely exist in natural bioactive substances. Two unprecedented reaction modes disclosed, the reactions could be readily scaled up. The protocol shows potential 1,2-diketone-mediated rapid construction complicated polycyclic scaffolds.

Language: Английский

Titanocene dichloride-catalyzed synthesis of heterocycles accelerated by in-situ formed Lewis and Brønsted acids DOI
Yuanyong Yao,

Li Tu,

Xiu Wang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114822 - 114822

Published: Jan. 18, 2025

Language: Английский

Citations

0

The Nazarov Reaction DOI

Emily Schmidt,

Seifeddine Khalifa,

F. G. West

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Recent Developments in Asymmetric Nazarov Reactions DOI

Hélène Pellissier

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(10), P. 757 - 776

Published: April 17, 2024

Abstract: The Nazarov reaction involves the cyclization of divinyl ketones into cyclopentenones under influence strong acids. prevalence five-membered carbocycles in a multitude natural and bioactive products has triggered an intense development efficient methods for their construction. In particular, asymmetric versions are achieved by using either chiral auxiliary or catalyst, which can be organocatalyst, metal multicatalytic system. This review aims to update field reactions published since 2017. It is divided four sections, dealing successively with auxiliaries, organocatalytic enantioselective reactions, metal/boron-catalyzed reactions. Each section subdivided simple Nazarov-based domino/tandem have allowed numerous more complex functionalized molecules synthesized one-pot procedures.

Language: Английский

Citations

2

Palladium-Catalyzed Synthesis of Indanone via C–H Annulation Reaction of Aldehydes with Norbornenes DOI

Wen-Xiu Lu,

Jiangang Mao, Xing Jian

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 784 - 792

Published: Dec. 14, 2023

A novel methodology for the synthesis of indanone derivates has been developed. The palladium-catalyzed annulation reaction o-bromobenzaldehydes with norbornene derivatives is achieved through extremely concise processes. skeleton was established directly via C–H activation aldehyde group under a mild condition. This method simple and practical, which simplified traditional rapid construction indanone.

Language: Английский

Citations

5

Switchable Enantioselectivity in Conjugate Alkyne Addition of β,γ-Unsaturated α-Keto Esters by Asymmetric Binary Acid Catalysis DOI

Depeng Duan,

Mengdie Tang,

Man Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3612 - 3616

Published: April 24, 2024

Switchable enantioselectivity was uncovered in the enantioselective catalytic conjugate addition of β,γ-unsaturated α-keto esters with terminal alkynes to chiral Lewis acid complex In(BF

Language: Английский

Citations

1

Cu(OTf)2–Phosphoric Acid-Catalyzed Tandem Oxa-Nazarov Cyclization and Dibromination of Conjugated 1,2-Diketones DOI

Hongchao Yin,

Yuan Tian, Chenxi Guo

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15862 - 15870

Published: Nov. 1, 2023

A facile tandem oxa-Nazarov cyclization and dibromination has been developed. The combination of Cu(OTf)2 diphenyl phosphate (DPP-H) was found to synergistically promote the coupling conjugated 1,2-diketones N-bromosuccinimide form 2,4-dibromo-3(2H)-furanones in good yields.

Language: Английский

Citations

2

Rapid Construction of Polycyclic Skeletons via Brønsted-Base-Catalyzed Annulations of Ethylidene 1,3-Indenediones and Vinyl 1,2-Diketones DOI

Lixuan Zhu,

Haotian Luo,

Jinggong Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 5893 - 5898

Published: July 9, 2024

Brønsted-base-catalyzed diversified annulations between ethylidene 1,3-indenediones and vinyl 1,2-diketones have been achieved, delivering three types of products containing oxabicyclo[3.2.1]octane, spiro[4.5]decane, branched triquinane skeletons, respectively, which widely exist in natural bioactive substances. Two unprecedented reaction modes disclosed, the reactions could be readily scaled up. The protocol shows potential 1,2-diketone-mediated rapid construction complicated polycyclic scaffolds.

Language: Английский

Citations

0