Highlighting the Rich Chemistry of the Allenone Moiety DOI Creative Commons
José M. Alonso, Pedro Almendros

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1332 - 1384

Published: March 14, 2023

Abstract Conjugated and non‐conjugated allenones appear as recurring motifs in organic synthesis, natural products mechanistic investigations showing unique properties applications. The ability of to build cycles has provided a direct access strained systems, medium‐sized rings, arenes, heterocycles complex polycycles. In addition, have served models catalysis. critic compilation herein presented will provide an exhaustive overview the synthetic possibilities may offer, which certainly inspire our community their search more efficient methodologies, preparation biological pharmaceutical targets, improve knowledge theoretical chemistry. Great part this review discuss aspects, catalysis innovation insights chemical transformations implying allenone motif. many examples on total synthesis pharmacologically active compounds be described. We hope that attractive chemistry, catalysis, medicinal chemistry communities. magnified image

Language: Английский

Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles DOI

Liangfeng Yang,

Liang Zeng,

Yanping Zhu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109685 - 109685

Published: March 1, 2024

Language: Английский

Citations

8

Three-Component Synthesis of Multiple Functionalized Allenes via Copper/Photoredox Dual Catalyzed 1,4-Alkylcyanation of 1,3-Enynes DOI

Yue Pu,

Shumin Ding, Hai‐Xia Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1834 - 1839

Published: Feb. 22, 2024

Efficient access to multiple functionalized allenes via a three component 1,4-alkylcyanation of enynes with cyclic alcohol derivatives in the presence trimethylsilyl cyanide (TMSCN) under copper/photoredox dual catalysis has been developed. Both easily transformable aldehyde and cyano groups were introduced tetra-substituted through light-induced C–C bond cleavage butanol pentanol derivatives. The reactions proceeded smoothly mild conditions broad functional tolerance.

Language: Английский

Citations

7

CF2Br2 as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis DOI
Lei Chen, Jingyi Wang, Lin Chen

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(38), P. 7047 - 7051

Published: Sept. 19, 2022

Commercially available CF2Br2 has been used as a convenient source for the rapid and reliable incorporation of gem-difluorovinyl motif into an allene framework via N-heterocyclic carbene catalyzed difluoroolefination 1,3-enynes. The reaction proceeds through cascade three-component radical relay/elimination process. This protocol is distinguished by its mild conditions, readily accessible starting materials, wide substrate scope, ease late-stage functionalization, thus unlocking untraditional strategy to construct new class functionalized allenes.

Language: Английский

Citations

28

Assembly of versatile fluorine-containing structures via N-heterocyclic carbene organocatalysis DOI
Bei Zhang, Jian Wang

Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(9), P. 1691 - 1703

Published: July 19, 2022

Language: Английский

Citations

26

Highlighting the Rich Chemistry of the Allenone Moiety DOI Creative Commons
José M. Alonso, Pedro Almendros

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1332 - 1384

Published: March 14, 2023

Abstract Conjugated and non‐conjugated allenones appear as recurring motifs in organic synthesis, natural products mechanistic investigations showing unique properties applications. The ability of to build cycles has provided a direct access strained systems, medium‐sized rings, arenes, heterocycles complex polycycles. In addition, have served models catalysis. critic compilation herein presented will provide an exhaustive overview the synthetic possibilities may offer, which certainly inspire our community their search more efficient methodologies, preparation biological pharmaceutical targets, improve knowledge theoretical chemistry. Great part this review discuss aspects, catalysis innovation insights chemical transformations implying allenone motif. many examples on total synthesis pharmacologically active compounds be described. We hope that attractive chemistry, catalysis, medicinal chemistry communities. magnified image

Language: Английский

Citations

16