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

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 9001 - 9010

Опубликована: Июнь 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.

Язык: 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, Год журнала: 2024, Номер 146(46), С. 32088 - 32097

Опубликована: Ноя. 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

Язык: Английский

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

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 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

Язык: Английский

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

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 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).

Язык: 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, Год журнала: 2024, Номер unknown, С. 110646 - 110646

Опубликована: Ноя. 1, 2024

Язык: Английский

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Recent advances in the synthesis of azetidines

Tetrahedron, Год журнала: 2024, Номер 169, С. 134383 - 134383

Опубликована: Ноя. 19, 2024

Язык: Английский

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