Theoretical investigation on the reaction mechanism and origin of stereoselectivity of a three-component coupling reaction under organocatalysis DOI

Yujian Yu,

Lujun Zhang, Yang Wang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114819 - 114819

Published: Jan. 6, 2025

Language: Английский

Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality DOI
Yan Xia,

Meiwen Liu,

Chenxiao Qian

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 30 - 34

Published: Nov. 14, 2022

Organocatalytic enantioselective construction of chiral spiro N , -acetal carbon stereocenters and axially 3-arylindoles has been achieved in one pot.

Language: Английский

Citations

26
Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis DOI Creative Commons
Marie Deliaval, Ramasamy Jayarajan, Lars Eriksson

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 10001 - 10006

Published: April 26, 2023

We have developed a new three-component catalytic coupling reaction of alkynyl boronates, diazomethanes, and aliphatic/aromatic ketones in the presence BINOL derivatives. The proceeds with remarkably high enantio- diastereoselectivity (up to three contiguous stereocenters) affording tertiary CF3-allenols single operational step. under mild, neutral, metal-free conditions, which leads level functional group tolerance.

Language: Английский

Citations

16
Pd((R)-DTBM-SEGphos)Cl2-catalyzed kinetic resolution of tertiary propargylic alcohols DOI Creative Commons
Jie Wang,

Wei‐Feng Zheng,

Yuling Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2477 - 2484

Published: Jan. 1, 2024

A variety of optically active tertiary propargylic alcohols and tetrasubstituted 2,3-allenoic acids have been synthesized via a Pd(( R )-DTBM-SEGphos)Cl 2 -catalyzed carboxylative kinetic resolution reaction racemic alcohols.

Language: Английский

Citations

5
Organocatalytic Enantioselective 1,12‐Addition of Alkynyl Biphenyl Quinone Methides Formed In Situ DOI
Xing Wang,

Boming Shen,

Meiwen Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(29)

Published: May 3, 2024

The chemistry of quinone methides formed in situ has been flourishing recent years. In sharp contrast, the development and utilization biphenyl are rare. this study, we achieved a remote stereocontrolled 1,12-conjugate addition for first time. presence suitable chiral phosphoric acid, alkynyl were generated from α-[4-(4-hydroxyphenyl)phenyl]propargyl alcohols, followed by enantioselective with indole-2-carboxylates. strategy enabled alcohols to serve as efficient allenylation reagents, providing practical access broad range axially allenes bearing (1,1'-biphenyl)-4-ol unit, which previously less accessible. Combined control experiments, density functional theory calculations shed light on reaction mechanism, indicating that enantioselectivity originates nucleophilic methides. Notably, not only versatile intermediates was confirmed but also organocatalytic 1,12-addition established.

Language: Английский

Citations

5
Organocatalytic Tandem Synthesis of Chiral Hexacyclic Bisindoles from Propargylic 3-Methyleneindoles with 2-Indolylmethanols DOI

Kanghua Rui,

Haorui Gu,

Alemayehu Gashaw Woldegiorgis

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6654 - 6658

Published: Sept. 6, 2023

A novel chiral phosphoric acid-catalyzed tandem regioselective 1,6-addition/double intramolecular nucleophilic addition annulation of the propargylic 3-methyleneindoles in situ generated from α-indolyl alcohols with 2-indolylmethanols has been developed. The methodology afforded new trifluoromethyl pentalenobisindoles bearing an all-carbon quaternary stereogenic center generally good yields excellent enantioselectivities.

Language: Английский

Citations

12
Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8‐Addition of Propargylic Aza‐p‐Quinone Methides DOI

Zhibin Yue,

Yan Xia,

Boming Shen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1078 - 1083

Published: Jan. 17, 2024

Abstract An organocatalytic remote stereocontrolled 1,8‐conjugated addition of in situ formed propargylic aza‐ p ‐QMs from α‐(4‐aminophenyl) alcohols and indole‐2‐carboxylates was developed, affording axially chiral tetrasubstituted allenes 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry ‐quinone methides, but also provides an alternative tool for preparation allenes.

Language: Английский

Citations

4
Palladium-catalyzed asymmetric [4 + 3] cycloaddition of methylene-trimethylenemethane: access to seven-membered exocyclic axially chiral allenes DOI Creative Commons
Yafei Wu, Zhuo Wang,

Yuqian Shan

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(25), P. 9703 - 9708

Published: Jan. 1, 2024

A palladium-catalyzed asymmetric [4 + 3] cycloaddition of the methylene-trimethylenemethane donor with an azadiene has been developed, affording benzofuro[3,2- b ]azepine-derived exocyclic chiral allene control axial and point chirality.

Language: Английский

Citations

4
A General Copper‐Box System for the Asymmetric Arylative Functionalization of Benzylic, Propargylic or Allenylic Radicals DOI Open Access

Peng‐Zi Wang,

Zhihan Zhang, Min Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 27, 2024

Abstract Radical‐involved arylative cross‐coupling reactions have recently emerged as an attractive strategy to access valuable aryl‐substituted motifs. However, there still exist several challenges such limited scope of radical precursors/acceptors, and lack general asymmetric catalytic systems, especially regarding the multicomponent variants. Herein, we reported a copper‐Box system for three‐component vinylarenes 1,3‐enynes, with oxime carbonates aryl boronic acids. The proceed under practical conditions in absence or presence visible‐light irradiation, affording chiral 1,1‐diarylalkanes, benzylic alkynes allenes good enantioselectivities. Mechanistic studies imply that copper/Box complexes play dual role both generation ensuing cross‐coupling. In cases irradiation could improve activity complex toward initial generation, enabling better efficiency match between formation

Language: Английский

Citations

4
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Visible Light-Driven Construction of Axially Chiral Heterocyclic Compounds DOI
Dong Liang,

Zi‐Wei He,

Jia‐Rong Chen

et al.

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0