Cited by Highly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations

Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers DOI

Yuheng Liu,

Lutong Yuan,

Linlong Dai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7630 - 7643

Published: May 13, 2024

Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed ethers via atroposelective esterification dialdehyde-containing ethers. NHC desymmetrization produces ether atropisomers with high yields and enantioselectivities moderate circumstances. Chiral compounds may precursors for highly functionalized bioactivity ligands catalysis.

Language: Английский

Citations

Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation DOI

Shaoqing Shi,

Chen‐Chang Cui,

Linlin Xu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 1, 2024

Language: Английский

Citations

Access to Chiral Dihydro-1,4-Benzoxazine-2-Carboxylates through NHC-Catalyzed Dynamic Kinetic Resolution DOI

Bin Liu, Qinqin Liu, Guanghong Wei

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

A chiral carbene-catalyzed dynamic kinetic resolution for the facile synthesis of enantioenriched dihydro-1,4-benzoxazine-2-carboxylates is disclosed. The reaction conditions are mild, and a diversity substituents well-tolerated in this transformation. In addition, our methodology also provides an efficient strategy building chromane-2-carboxylate 2,3-dihydro-1,4-benzodioxane-2-carboxylate. optically pure products generated from protocol can be easily derived as key intermediates drugs bioactive molecules.

Language: Английский

Citations

NHC‐Catalyzed Remote γ,δ–Protonation and Formal [3+3] Annulation to Access Functionalized Dihydropyridinones DOI

Chengxian Yang,

A. V. Pan, Jing Qi

et al.

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Abstract We have developed an N ‐heterocyclic carbene (NHC)‐catalyzed [3+3] annulation of α,β−γ,δ‐unsaturated aldehydes with enamines for the asymmetric synthesis dihydropyridinone that bearing all‐carbon quaternary center. This strategy proceeding via NHC‐mediated γ,δ–protonation α,β−γ,δ−unsaturated aldehydes, followed by cycloadditions. protocol delivers a wide range substituited dihydropyridinones in good yields excellent enantioselectivities.

Language: Английский

Citations

Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI

Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Citations

Enantioselective S_N2 Alkylation of Homoenolates by N‐Heterocyclic Carbene Catalysis DOI

En Li, Kai Tang,

Zhuhui Ren

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 10(29)

Published: Aug. 4, 2023

The functionalization of the β-carbon enals with electrophiles is a signature umpolung reactivity N-heterocyclic carbene (NHC) derived homoenolates. However, only limited number are shown to be compatible, most them being π-electrophiles. In this study, successful enantioselective β-alkylation homoenolates reported using Csp3 through an SN 2 strategy. protocol shows broad scope regarding alkyl electrophiles, delivering good yields, and excellent enantioselectivities (up 99% ee). It enables installation drug-like structural motifs in either or alkylating agents, demonstrating its potential as valuable tool for late-stage modification. Furthermore, concise synthetic route presented chiral pyrroloindoline-type skeletons. Preliminary mechanistic studies support direct mechanism.

Language: Английский

Citations

Highly Enantioselective Construction of the Polycyclic Piperazin-2-ones via NHC-Catalyzed [12 + 2] Cycloadditions DOI

Xiaojie Ren, Xiaoyong Duan, Yanting Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7917 - 7922

Published: Oct. 24, 2023

NHC-catalyzed diastereoselective and enantioselective [12 + 2] higher-order cycloadditions of 5H-benzo[a]-pyrrolizine-3-carbaldehydes with cyclic sulfonic imines are described. Various optically pure polycyclic piperazin-2-ones were successfully constructed under mild reaction conditions excellent diastereoselectivities enantioselectivities. The generated chiral could be transformed to planar-chiral nine-membered amides via squaramide-catalyzed asymmetric ring-expansion reactions.

Language: Английский

Citations

Highly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations DOI

Xiaojie Ren, Xiaoyong Duan,

Yuxuan Feng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

The NHC-catalyzed enantioselective [4 + 2] annulation of 9

Language: Английский

Citations