Tetrahedron Chem, Год журнала: 2024, Номер unknown, С. 100118 - 100118
Опубликована: Дек. 1, 2024
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(38)
Опубликована: Июнь 26, 2024
Piperidines are widely present in small molecule drugs and natural products. Despite many methods have been developed for their synthesis, new approaches to polysubstituted piperidines highly desirable. This work presents a radical (4+2) cycloaddition reaction synthesis of featuring dense substituents at 3,4,5-positions that not readily accessible by known methods. Using commercially available diboron(4) compounds 4-phenylpyridine as the catalyst precursors, boronyl radical-catalyzed between 3-aroyl azetidines various alkenes, including previously unreactive 1,2-di-, tri-, tetrasubstituted has delivered generally high yield diastereoselectivity. The also features modularity, atom economy, broad substrate scope, metal-free conditions, simple catalysts operation. utilization products demonstrated selective transformations. A plausible mechanism, with ring-opening azetidine rate-limiting step, proposed based on experimental computational results.
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2024, Номер 26(33), С. 7021 - 7025
Опубликована: Авг. 14, 2024
Cyclopentene skeletons are ubiquitous in natural products and small molecule drugs. The (3 + 2) cycloaddition of cyclopropanes alkynes represents an efficient atom-economic strategy for synthesizing these structures. However, the types substituents on cyclopropane alkyne used previous works show evident limitations, restricting application this type reaction to some extent. Herein, we report a broad-scope catalyzed by boronyl radicals. In method, various substrates, such as mono-, di-, tri-, tetrasubstituted cyclopropanes, well mono- disubstituted alkynes, were compatible with up 98% isolated yield.
Язык: Английский
Процитировано
4
ChemistrySelect, Год журнала: 2025, Номер 10(9)
Опубликована: Март 1, 2025
Abstract Over the last decade, there have been notable advances in field of ring opening reaction numerous cyclopropane derivatives under metal‐free conditions including donor–acceptor cyclopropanes, acceptor‐activated alkylidenecyclopropanes, cyclopropyl alcohols, and vinylidenecyclopropanes. This review article aims to offer a comprehensive overview on cleavage reactions cyclopropanes using Bronsted Lewis acids, organic inorganic bases, TCT‐DMF, ionic liquids etc. Photoinduced catalyst‐free are also accentuated this review.
Язык: Английский
Процитировано
0
Angewandte Chemie, Год журнала: 2024, Номер 136(38)
Опубликована: Июнь 26, 2024
Abstract Piperidines are widely present in small molecule drugs and natural products. Despite many methods have been developed for their synthesis, new approaches to polysubstituted piperidines highly desirable. This work presents a radical (4+2) cycloaddition reaction synthesis of featuring dense substituents at 3,4,5‐positions that not readily accessible by known methods. Using commercially available diboron(4) compounds 4‐phenylpyridine as the catalyst precursors, boronyl radical‐catalyzed between 3‐aroyl azetidines various alkenes, including previously unreactive 1,2‐di‐, tri‐, tetrasubstituted has delivered generally high yield diastereoselectivity. The also features modularity, atom economy, broad substrate scope, metal‐free conditions, simple catalysts operation. utilization products demonstrated selective transformations. A plausible mechanism, with ring‐opening azetidine rate‐limiting step, proposed based on experimental computational results.
Язык: Английский
Процитировано
0
Tetrahedron Chem, Год журнала: 2024, Номер unknown, С. 100118 - 100118
Опубликована: Дек. 1, 2024
Язык: Английский
Процитировано
0