Photoinduced Cobalt-Catalyzed Desymmetrization of Dialdehydes to Access Axial Chirality

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(12), P. 6944 - 6952

Published: March 15, 2023

Enantioselective metallaphotoredox catalysis, which combines photoredox catalysis and asymmetric transition-metal has become an effective approach to achieve stereoconvergence under mild conditions. Although many impressive synthetic approaches have been developed access central chirality, the construction of axial chirality by still remains underexplored. Herein, we report two visible light-induced cobalt-catalyzed reductive couplings biaryl dialdehydes synthesize axially chiral aldehydes (60 examples, up 98% yield, >19:1 dr, >99% ee). This protocol shows good functional group tolerance, broad substrate scope, excellent diastereo- enantioselectivity.

Language: Английский

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Transition-metal-catalyzed atroposelective synthesis of axially chiral styrenes

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(85), P. 12669 - 12684

Published: Jan. 1, 2023

Recent advances in the asymmetric synthesis of axially chiral styrenes catalyzed by transition metals were summarized.

Language: Английский

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Catalytic atroposelective synthesis

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(5), P. 483 - 498

Published: April 30, 2024

Language: Английский

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Beyond conventional: Role of chiral metal–organic frameworks in asymmetric scenarios

Nano Today, Journal Year: 2024, Volume and Issue: 56, P. 102227 - 102227

Published: March 18, 2024

Language: Английский

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Developing Biarylhemiboronic Esters for Biaryl Atropisomer Synthesis via Dynamic Kinetic Atroposelective Suzuki–Miyaura Cross-Coupling

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(9), P. 6283 - 6293

Published: Feb. 21, 2024

We herein introduce biarylhemiboronic esters as a new type of bridged biaryl reagent for asymmetric synthesis axially chiral structures, and the palladium-catalyzed Suzuki-Miyaura cross-coupling is developed. This dynamic kinetic atroposelective coupling reaction exhibits high enantioselectivity, good functional group tolerance, broad substrate scope. The synthetic application current method was demonstrated by transformations product programmed polyarene. Preliminary mechanistic studies suggested that proceeded via an enantio-determining transmetalation step.

Language: Английский

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Atroposelective catalysis

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(7), P. 497 - 517

Published: June 18, 2024

Language: Английский

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An Enantioselective Suzuki–Miyaura Coupling To Form Axially Chiral Biphenols

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(33), P. 15026 - 15032

Published: Aug. 15, 2022

Axial chirality features prominently in molecules of biological interest as well chiral catalyst designs, and atropisomeric 2,2′-biphenols are particularly prevalent. Atroposelective metal-catalyzed cross-coupling is an attractive modular approach to access enantioenriched biphenols, yet existing protocols cannot achieve this directly. We address challenge through the use enantiopure, sulfonated SPhos (sSPhos), ligand that has until now been used only racemic form derives its from axis introduced sulfonation. believe noncovalent interactions involving sulfonate group responsible for high levels asymmetric induction we obtain 2,2′-biphenol products Suzuki–Miyaura coupling, have developed a highly practical resolution sSPhos via diastereomeric salt recrystallization.

Language: Английский

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Desymmetrization of Vicinal Bis(boronic) Esters by Enantioselective Suzuki–Miyaura Cross-Coupling Reaction

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(15), P. 8308 - 8313

Published: April 6, 2023

The development of an enantioselective catalytic Suzuki-Miyaura reaction that applies to

Language: Английский

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Enantioselective Rhodium‐Catalyzed C−H Arylation Enables Direct Synthesis of Atropisomeric Phosphines

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(8)

Published: Jan. 6, 2024

Atropisomeric phosphines hold considerable significance in asymmetric catalysis, yet their synthesis presents a formidable challenge owing to intricate multistep procedures. In this context, groundbreaking methodology has been presented for preparation. This innovative approach entails an atroposelective rhodium-catalyzed C-H activation employing aryl and heteroaryl halides, chelated by P(III) center. The essence of strategy lies its ability directly construct chiral phosphine ligands single step, thereby exhibiting exceptional efficiency terms atom redox economy. Illustrative examples serve demonstrate the immense potential situ-formed catalysis. Mechanistic experiments have further provided invaluable insights into transformation.

Language: Английский

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Indium nanocubes based recyclable fluorescent chemosensor for sustainable environmental monitoring: pH-induced fluorescence transition and selective detection of Pd(II) ions

The Science of The Total Environment, Journal Year: 2024, Volume and Issue: 920, P. 171043 - 171043

Published: Feb. 16, 2024

Language: Английский

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