Organocatalyzed Asymmetric [2+2] Cycloaddition of Saccharin-Derived Endocyclic Ketimines and Allenoates for the Synthesis of Fused Azetidines

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100133 - 100133

Published: May 1, 2025

Language: Английский

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Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9001 - 9010

Published: June 6, 2024

2,3-Allenamides are an important class of unsaturated group-substituted carbonyl compounds. A palladium-catalyzed aminocarbonylation propargyl acetates with amines for the synthesized tri-/tetrasubstituted 2,3-allenamides has been developed. broad range have prepared from in good to excellent yields. The reaction featured mild conditions and functional group tolerance. applicability this methodology was further highlighted by late-stage modification several natural products pharmaceuticals.

Language: Английский

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Catalytic Asymmetric Reactions of Ketimines and Alkenes via [2 + 2] Cycloaddition: Chemical Reactivity Controlled by Switching a Heteroatom

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(46), P. 32088 - 32097

Published: Nov. 8, 2024

Azetidine units are commonly found in natural products and biologically active drugs. The [2 + 2] cycloaddition of imines alkenes has been extensively used the synthesis such structures, while enantioselective approaches remain elusive. Herein, an efficient B(C

Language: Английский

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Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Chiral 2-azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70-98 % yields up to 96 ee) through phosphine-catalyzed [2+2] annulation yne-enones with sulfamate-derived cyclic imines. These were easily transformed into upon treatment Et

Language: Английский

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Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Chiral 2‐azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70–98 % yields up to 96 ee) through phosphine‐catalyzed [2+2] annulation yne‐enones with sulfamate‐derived cyclic imines. These were easily transformed into upon treatment Et 3 SiH, BF ⋅ 2 O water at rt for minutes. Based on the above transformations, a concise one‐pot synthetic procedure combining imines under phosphine catalysis sequential reduction/isomerization/ring‐opening reaction was thus set up, providing axially tetrasubstituted satisfactory enantioselectivities (56–90 91 ee).

Language: Английский

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DABCO-catalyzed [3 + 4] annulations of Schiff bases with α-substituted allenes: Construction of functionalized benzazepine derivatives

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110646 - 110646

Published: Nov. 1, 2024

Language: Английский

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Recent advances in the synthesis of azetidines

Tetrahedron, Journal Year: 2024, Volume and Issue: 169, P. 134383 - 134383

Published: Nov. 19, 2024

Language: Английский

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