2009
DOI: 10.1021/jo802531h
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Stereoselective One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyran via Prins−Friedel−Crafts Reaction

Abstract: A diastereoselective one-pot, three-component Prins-Friedel-Crafts reaction was developed for the synthesis of 4-aryltetrahydropyran derivatives from the reaction of carbonyl compounds with homoallylic alcohol in the presence of arene promoted by boron trifluoride etherate.

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Cited by 62 publications
(19 citation statements)
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“…In our recent work we have generated oxocarbenium ion and then trapped by nucleophiles such as arene [11]. Our initial attempt to generate oxocarbenium ion from DHA using BF 3 ·Et 2 O and then trap by nucleophiles such as acetonitrile and arene failed (Scheme ).…”
Section: Resultsmentioning
confidence: 99%
“…In our recent work we have generated oxocarbenium ion and then trapped by nucleophiles such as arene [11]. Our initial attempt to generate oxocarbenium ion from DHA using BF 3 ·Et 2 O and then trap by nucleophiles such as acetonitrile and arene failed (Scheme ).…”
Section: Resultsmentioning
confidence: 99%
“…Eleven examples were investigated under mild conditions; atom efficiency and good substrate scope was seen to show moderate to good yields. [65] Condensation of 3-aminocoumarin with 4-nitrobenzaldehyde afforded 2-azadienes, which were then reacted with various electron-rich alkenes (10 examples [68] Aromatic aldehydes containing electron-withdrawing groups and simple benzaldehyde afforded better yields relative to electron-donating groups. Saturated aliphatic aldehydes are found to be better substrates Scheme than the conjugated aliphatic aldehydes.…”
Section: Heterocycles With One Heteroatommentioning
confidence: 99%
“…Green chemistry approaches are significant due to the reduction in byproducts, reduction in produced waste, and reduction of energy cost. The possibility of performing multicomponent reactions under solvent-free conditions with a heterogeneous catalyst could enhance their efficiency from an economic as well as an ecological point of view [15]. …”
Section: Introductionmentioning
confidence: 99%