Synthesis of Furans through Silver-Catalyzed Propargyl-Claisen Rearrangement Followed by Cyclocondensation

Autor:	Stefan F. Kirsch, Adeline Palisse
Rok vydání:	2014
Předmět:	Claisen rearrangement chemistry.chemical_compound chemistry Cascade reaction Furan Organic Chemistry Propargyl Organic chemistry Homogeneous catalysis Physical and Theoretical Chemistry Sigmatropic reaction Isomerization Catalysis
Zdroj:	European Journal of Organic Chemistry. 2014:7095-7098
ISSN:	1434-193X
DOI:	10.1002/ejoc.201402983
Popis:	The generation of highly substituted furans from propargyl vinyl ethers bearing a free hydroxy group was investigated. In the presence of catalytic amounts of AgBF4, a formal [3,3] sigmatropic rearrangement takes place in the first stage of the sequence. The resulting allenyl carbonyl intermediates then undergo cyclocondensation, which upon double-bond isomerization leads directly to the five-membered heterocyclic products. This domino reaction allows the synthesis of various tri- and tetrasubstituted furan products; an example leading to pyrroles in an analogous way is also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fee45656a09b3590415aef908517f998 https://doi.org/10.1002/ejoc.201402983 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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