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Recent advances in organocatalytic atroposelective reactions.
Beilstein J Org Chem
January 2025
Department of Organic Chemistry, Faculty of Natural Science, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia.
Axial chirality is present in a variety of naturally occurring compounds, and is becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of axially chiral compounds via asymmetric organocatalysis.
View Article and Find Full Text PDFN-Heterocyclic carbene (NHC) organocatalysis: from fundamentals to frontiers.
Chem Soc Rev
February 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
N-Heterocyclic carbenes (NHCs) have been used as organocatalysts for a multitude of C-C and C-heteroatom bond-forming reactions. They enable diverse modalities of activating a wide range of structurally distinct substrate classes and allow access to electronically distinct intermediates. The easy tunability of the NHC scaffold contributes to its versatility.
View Article and Find Full Text PDFSynthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3-Indolylmethanols.
Angew Chem Int Ed Engl
October 2024
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China.
Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery of their applications have become significant but challenging issues in the scientific community due to the unique structures of this class of atropisomers. We herein report the first catalytic atroposelective preparation of cyclopentenyl[b]indoles, a new kind of alkene atropisomers, with stereogenic point and axial chirality via an unusual rearrangement reaction of 3-indolylmethanols under asymmetric organocatalysis. Notably, this novel type of alkene atropisomers have promising applications in developing chiral ligands or organocatalysts, discovering antitumor drug candidates and fluorescence imaging materials.
View Article and Find Full Text PDFOrganocatalytic enantioselective synthesis of C-N atropisomers formal C-O bond amination.
Chem Sci
March 2024
Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology Guangming Advanced Research Institute, Southern University of Science and Technology (SUSTech) Shenzhen 518055 China
Compared with well-developed construction of C-C atropisomers, the synthesis of C-N atropisomers remains in its infancy, which is recognized as both appealing and challenging. Herein, we achieved the first organocatalyzed asymmetric synthesis of C-N atropisomers by formal C-O amination. With the aid of a suitable acid, 3-alkynyl-3-hydroxyisoindolinones reacted smoothly with 1-methylnaphthalen-2-ols to afford a wide range of atropisomers by selective formation of the C-N axis.
View Article and Find Full Text PDFEnantioselective Synthesis of C-O Axially Chiral Diaryl Ethers by NHC-Catalyzed Atroposelective Desymmetrization.
Angew Chem Int Ed Engl
December 2023
Department of Organic Chemistry, Indian Institute of Science, 560012, Bangalore, India.
Axially chiral diaryl ethers, a distinguished class of atropisomers possessing unique dual C-O axis, hold immense potential for diverse research domains. In contrast to the catalytic enantioselective synthesis of conventional single axis bearing atropisomers, the atroposelective synthesis of axially chiral ethers containing flexible C-O axis remains a significant challenge. Herein, we demonstrate the first N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers.
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