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Synthesis 2024; 56(24): 3741-3751
DOI: 10.1055/a-2369-3961
DOI: 10.1055/a-2369-3961
feature
Recent Advancements in The Chemistry of Diazo Compounds
Mild and Stereoselective Synthesis of (1E,3E)-Dienes through Silver(I)-Catalyzed β-Hydride Migration from Allylic α-Diazo Esters
We are grateful to the Brazilian governmental agencies CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico), and FAPESC (Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina) for the research grants and fellowships. Support from INCT-Catálise/FAPESC/CNPq/CAPES is also gratefully acknowledged.
Abstract
A mild procedure for the diastereoselective preparation of functionalized 1,3-dienes and their synthetic versatility are described herein. The silver-catalyzed decomposition of α-diazo-γ,δ-unsaturated esters through β-hydride migration at room temperature resulted in the stereoselective formation of 12 conjugated (1E,3E)-dienes. Further synthetic post-modifications included intramolecular Heck reaction and hydrogenation, leading to a novel substituted indene and an aliphatic diester, respectively. To rationalize the observed reaction outcome, a computational investigation of the mechanisms was conducted, emphasizing the importance of factors such as metallocarbenoid stability, substituent effects, and microkinetics simulations to better understand the reaction intricacies.
Key words
α-diazo carbonyl compounds - silver-catalyzed reaction - β-hydride migration - 1,3-dienes - stereoselective catalysis - computational methodsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2369-3961.
- Supporting Information
Publication History
Received: 18 June 2024
Accepted after revision: 18 July 2024
Accepted Manuscript online:
18 July 2024
Article published online:
13 August 2024
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