Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Language: Английский

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Enhanced Pyridine-Oxazoline Ligand-Enabled Pd(II)-Catalyzed Aminoacetoxylation of Alkenes for the Asymmetric Synthesis of Biaryl-Bridged 7-Membered N-Heterocycles and Atropisomers

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

A new class of binaphthyl unit-enhanced pyridine-oxazoline ligands was developed to promote the Pd-catalyzed enantioselective intramolecular 7-exo aminoacetoxylation unactivated biaryl alkenes. Biaryl-bridged 7-membered N-heterocycles bearing a chiral center were obtained in good yields with excellent enantioselectivities (up 99:1 er). Computational investigations on series biaryl-bridged rings provided insights into rotational barrier potentially unit by substituent effect including heteroatom, protecting group, and center. The kinetic resolution racemic axially biaryls via alkenes has also been achieved, affording previously inaccessible both axis, as well amino alcohols.

Language: Английский

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Synthesis of All Ring Sizes of Medium-Sized Heterocycles Bridged Biaryls via VQM-Enabled Diversity-Oriented Synthetic Strategy

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

Herein, for the first time, controllable, accurate, and diverse synthesis of all ring sizes medium-sized (8- to 11-membered) indole-derived bridged biaryls has been realized by using ingeniously designed o-alkynylnaphthols that feature cyclic amines with adjustable sizes. The transformation may proceed through a DBN-mediated in-situ generation vinylidene ortho-quinone methides/indole-ring formation/ring expansion cascade sequence, which is characterized acceptable excellent yields good functional group tolerance.

Language: Английский

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Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 5, 2025

Photoredox catalysis has emerged as a powerful tool for forming and breaking chemical bonds, further taking hold with its integration asymmetric catalysis. While the dual-catalytic approach led to successful examples of control stereogenic centers, axes remained underexplored. In this study, an acylimine intermediate was generated through photoredox catalysis, symmetric substrate, 2-arylresorcinol, desymmetrized aid chiral phosphoric acid Using approach, center axis were successfully controlled provide natural-product-driven compound. The origins enantioselectivity diastereoselectivity investigated density functional theory study four possible enantiodetermining transition states. Consequently, first total syntheses ring-contracted naphthylisoquinoline alkaloid ancistrobrevolines A B accomplished concisely. This provides not only novel methodology strategy synthesize alkaloids but also direction advance catalytic research synthesis studies.

Language: Английский

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Cp*Ir-SPDO Catalyzed Asymmetric Intramolecular Amination via Nitrene Transfer toward Chiral Spiro-Quaternary Indolinone

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(8), P. 2605 - 2605

Published: Jan. 1, 2024

Language: Английский

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De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Language: Английский

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