Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols DOI
Ping Wu,

Wen‐Tao Zhang,

Jixiang Yang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(42)

Published: July 23, 2024

Abstract Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery their applications have become significant but challenging issues in the scientific community due to unique structures this class atropisomers. We herein report first catalytic atroposelective cyclopentenyl[ b ]indoles, a new kind atropisomers, point axial chirality via an unusual rearrangement reaction 3‐indolylmethanols under asymmetric organocatalysis. Notably, novel type promising developing chiral ligands or organocatalysts, discovering antitumor drug candidates fluorescence imaging materials. Moreover, theoretical calculations elucidated possible mechanism non‐covalent interactions control enantioselectivity. This approach offers synthetic strategy for elements, represents 3‐indolylmethanols, which will advance chemistry indole chemistry.

Language: Английский

Copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with vinyl cations DOI
Ze‐Shu Wang,

Hao-Jin Xu,

Yang‐Bo Chen

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(100), P. 14831 - 14834

Published: Jan. 1, 2023

A copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with diynes has been developed, affording axially chiral arylpyrroles bearing 1,3-dioxole moieties high enantioselectivities under mild conditions.

Language: Английский

Citations

2
Enantioselective Reaction of Diynes and Multiynes for the Synthesis of Axially Chiral Compounds DOI
Xin‐Qi Zhu, Yuchao Li, Long‐Wu Ye

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 29, 2023

Abstract Diynes and multiynes have proven to versatile synthons for the synthesis of a range useful cyclic compounds, especially functionalized complicated polycyclic skeletons comprising carbocycles heterocycles. Axially chiral one most significant class compounds featuring axial chirality, are widely existed in natural products pharmaceuticals as well ligands catalysts. Over past decades, numerous synthetic protocols been established atroposelective axially compounds. However, catalytic asymmetric reaction diynes has rarely investigated there is no systematic brief up now. In this review, we summarize advances attainments construction also propose remained challenges opportunities future breakthroughs field.

Language: Английский

Citations

2
Modular Access to Tetrasubstituted N−H Pyrroles by Catalytic 1,3‐Dipolar Cycloaddition of Azomethine Ylides and α,β‐Ynones DOI
Qian Huang,

Zi‐Han Li,

Zhen‐Ni Zhao

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(30)

Published: April 26, 2024

Abstract The development of efficient synthetic strategies for the preparation tetrasubstituted N−H pyrrole derivatives, especially in an environmentally benign fashion is important yet challenging. Herein, we report a copper(II)‐catalyzed tandem reaction involving 1,3‐dipolar cycloaddition α,β‐ynones and glycine iminoesters, followed by copper(II)‐promoted oxidative (air) dehydrogenative aromatization, allowing de novo access to pyrroles up 81 % yield under green conditions. A possible pathway tentatively proposed. Finally, fully substituted are available N‐alkylation, preliminary phase‐transfer catalytic asymmetric N‐alkylation was also studied give axially chiral pyrrole.

Language: Английский

Citations

0
Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides DOI
Xin‐Qi Zhu,

Hai‐Yu Yang,

Long‐Wu Ye

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Language: Английский

Citations

0
Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols DOI
Ping Wu,

Wen‐Tao Zhang,

Jixiang Yang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(42)

Published: July 23, 2024

Abstract Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery their applications have become significant but challenging issues in the scientific community due to unique structures this class atropisomers. We herein report first catalytic atroposelective cyclopentenyl[ b ]indoles, a new kind atropisomers, point axial chirality via an unusual rearrangement reaction 3‐indolylmethanols under asymmetric organocatalysis. Notably, novel type promising developing chiral ligands or organocatalysts, discovering antitumor drug candidates fluorescence imaging materials. Moreover, theoretical calculations elucidated possible mechanism non‐covalent interactions control enantioselectivity. This approach offers synthetic strategy for elements, represents 3‐indolylmethanols, which will advance chemistry indole chemistry.

Language: Английский

Citations

0