Enantioselective Synthesis of Heteroatom‐Linked Non‐Biaryl Atropisomers

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(30)

Published: May 15, 2024

Atropisomers hold significant fascination, not only for their prevalence in natural compounds but also biological importance and wide-ranging applications as chiral materials, ligands, organocatalysts. While biaryl heterobiaryl atropisomers are commonly studied, the enantioselective synthesis of less abundant heteroatom-linked non-biaryl presents a formidable challenge modern organic synthesis. Unlike classical atropisomers, these molecules allow rotation around two bonds, resulting low barriers to enantiomerization through concerted bond rotations. In recent years discovery new configurationally stable rare scaffolds such aryl amines, ethers sulfones well innovative methodologies control configuration have been disclosed literature constitute topic this minireview.

Language: Английский

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Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

Axially chiral diaryl ethers represent a distinct class of atropisomers, characterized by unique dual C─O axes system, which have been found in variety natural products, pharmaceuticals, and ligands. However, the catalytic enantioselective synthesis these atropoisomers poses significant challenges, due to difficulty controlling both axes, their more flexible conformations. Herein, an efficient protocol for axially is presented using organocatalyzed asymmetric Povarov reaction-enabled desymmetrization, followed aromatizations. This method yields wide range novel quinoline-based ether good high enantioselectivities. Notably, various aromatization protocols are developed, resulting diverse set polysubstituted quinoline-containing atropisomers. Thermal racemization studies suggested excellent configurational stabilities atropisomers (with barriers up 38.1 kcal mol

Language: Английский

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Evolution in the asymmetric synthesis of biaryl ethers and related atropisomers

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(54), P. 6837 - 6846

Published: Jan. 1, 2024

Axially chiral biaryl ethers and related compounds hold valuable potential in natural products, medicinal chemistry, catalysis; however, their asymmetric syntheses have always been overlooked compared to other biaryl/hetero-biaryl atropisomers. Unlike the later class molecules bearing a single axis, former category possesses unique type of atropisomerism two axes. Due great importance diverse research domains, catalytic atropselective ether synthesis has recently witnessed an upsurge. This highlight article provides elaborated view on developments synthetic methods that explored achieve dual axial chirality scaffolds.

Language: Английский

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Enantioselective Synthesis of Heteroatom‐Linked Non‐Biaryl Atropisomers

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(30)

Published: May 15, 2024

Abstract Atropisomers hold significant fascination, not only for their prevalence in natural compounds but also biological importance and wide‐ranging applications as chiral materials, ligands, organocatalysts. While biaryl heterobiaryl atropisomers are commonly studied, the enantioselective synthesis of less abundant heteroatom‐linked non‐biaryl presents a formidable challenge modern organic synthesis. Unlike classical atropisomers, these molecules allow rotation around two bonds, resulting low barriers to enantiomerization through concerted bond rotations. In recent years discovery new configurationally stable rare scaffolds such aryl amines, ethers sulfones well innovative methodologies control configuration have been disclosed literature constitute topic this minireview.

Language: Английский

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Synthesis of Amino Acids with Axially Chiral Diaryl Ethers Units

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0780 - 0780

Published: June 14, 2024

Language: Английский

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