Synthesis of Chiral β,β-Disubstituted Ketones via CuH-Catalyzed Coupling of Aryl Alkenes and 3-Aryl-2H-azirines DOI
Fang Xie,

Shijie Dong,

Yajun Sun

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8213 - 8217

Published: Nov. 2, 2022

A CuH-catalyzed coupling of aryl alkenes with 3-aryl-2H-azirines has been developed to synthesize optically active β,β-disubstituted ketones. We propose that this protocol occurs through a sequence in which chiral alkylcopper complex regioselectively attacks the N-C2 bonds azirines generate β-aryl imines, additionally afford ketones upon hydrolysis. This method provides novel complementary approach for synthesizing good yields high levels enantioselectivity under mild conditions.

Language: Английский

Recent advances in ligand-enabled palladium-catalyzed divergent synthesis DOI
Yue Wang,

Jinzan Feng,

Er‐Qing Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 37 - 54

Published: Nov. 27, 2023

Developing efficient and straightforward strategies to rapidly construct structurally distinct diverse organic molecules is one of the most fundamental tasks in synthesis, drug discovery materials science. In recent years, divergent synthesis functional from same starting has attracted significant attention been recognized as an powerful strategy. To achieve this objective, proper adjustment reaction conditions, such catalysts, solvents, ligands, etc., required. review, we summarized efforts chemo-, regio- stereodivergent reactions involving acyclic cyclic systems catalyzed by palladium complexes. Meanwhile, types, including carbonylative reactions, coupling cycloaddition well probable mechanism have also highlighted detail.

Language: Английский

Citations

14
Palladium-Catalyzed Divergent Synthesis from o-Sulfonamido Trifluoroacetophenones and 2-En-4-ynyl Carbonates DOI

Meng-Qi Gan,

Jian‐Xiang Zhu,

Zhichao Chen

et al.

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

Published: Feb. 15, 2025

Here we present a palladium-catalyzed divergent transformative reaction between o-sulfonamido trifluoroacetophenones and 2-en-4-ynyl carbonates. A spectrum of enantioenriched 2,5-dihydrofuran-fused tetrahydroquinolines bearing either (Z)- or (E)-exocyclic double bond are constructed with moderate to high enantioselectivity from 5-aryl-substituted carbonates by tuning palladium sources, while analogous 2,3-dihydrofuran-fused products furnished using 5-alkyl-substituted ones.

Language: Английский

Citations

0
Substituted 2H-azirine derivatives - Versatile reagents to access skeletal diversity DOI

Mahsa Farivar,

Reihane Peirow,

Aida Iraji

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 142148 - 142148

Published: March 1, 2025

Language: Английский

Citations

0
Enantio- and Diastereoselective Copper-Catalyzed Synthesis of Chiral Aziridines with Vicinal Tetrasubstituted Stereocenters DOI
Fang Xie, Jie Zhao,

Deyue Ren

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8530 - 8534

Published: Nov. 17, 2023

A Cu-catalyzed coupling of cyclic imino esters with 2H-azirines has been developed to synthesize novel optically active aziridines in high yields excellent levels diastereo- and enantioselectivities under mild conditions. This protocol features a broad substrate scope good functional group compatibility, it enriches the existing reaction type rapid synthesis bearing vicinal tetrasubstituted stereogenic carbon centers.

Language: Английский

Citations

6
Copper-Catalyzed Coupling of N-Phenoxyacetamides and 2H-Azirines for Synthesis of α-Amino Oxime Ethers DOI

Yuelu Zhu,

Jiao Chen, Jie Yan

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(20), P. 3393 - 3401

Published: May 19, 2023

Abstract Copper-catalyzed coupling reaction involving N-phenoxyacetamides and 2H-azirines is described, in which N–O C–N bonds are broken restructured. This protocol provides an efficient strategy for the highly regioselective synthesis of racemic α-amino oxime ethers. In addition, this can be used to modify natural products gram-scale compatible.

Language: Английский

Citations

4
Pd-Catalyzed Chemodivergent Synthesis of 1-Indanones via Diethyl Zinc-Mediated Precise Switching of Umpolung Reactivity DOI

Suman Sar,

Prasanta Ghorai

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(14), P. 9706 - 9712

Published: July 10, 2023

Herein, we unveiled an efficient intramolecular umpolung chemodivergent cascade route for synthesizing 1-indanones via precisely switching the reactivity between α-diketone and π-allyl Pd complex. This successful merging of strategies is accomplished by employing a catalyst Et2Zn, which provides broad array with good yield selectivity. The salient feature involves amphiphilic behaviors both allyl functionality in two engineered mild reaction conditions. Furthermore, scale up synthesis postsynthetic transformations amplify significance current protocol. Additionally, have achieved diastereomers ether alcohol derivatives 1-indanone efficiently synthetic transformation.

Language: Английский

Citations

3
Synthesis of Chiral β,β-Disubstituted Ketones via CuH-Catalyzed Coupling of Aryl Alkenes and 3-Aryl-2H-azirines DOI
Fang Xie,

Shijie Dong,

Yajun Sun

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8213 - 8217

Published: Nov. 2, 2022

A CuH-catalyzed coupling of aryl alkenes with 3-aryl-2H-azirines has been developed to synthesize optically active β,β-disubstituted ketones. We propose that this protocol occurs through a sequence in which chiral alkylcopper complex regioselectively attacks the N-C2 bonds azirines generate β-aryl imines, additionally afford ketones upon hydrolysis. This method provides novel complementary approach for synthesizing good yields high levels enantioselectivity under mild conditions.

Language: Английский

Citations

3