A simple route to selective Diels-Alder reactions using modified zeolite Y

Chemistry Letters

Volumn , Issue 4, 2000, Pages 358-359

  Najafi, H Mahmoudi ^a   Ghandi, M ^a   Farzaneh, F ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ALZAHRA UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034341146     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.358     Document Type: Article

References (24)

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21. Due to the presence of methyl groups in MA and MVK and their simple characterization in NMR spectra we used the NMR method to obtain the endo:exo ratio and the ee of the products using chiral shift reagent.
22. Loading procedure: The zeolites were exchanged by the chiral compound according to the reported procedure (reference 13). The vacuum dried zeolite was added to the dienophile (1 mmol) solution in n-hexane (zeolite:dienophile weight ratio = 25:1) and the mixture was stirred at room temperature for 3 h. After filtration and washing with n-hexane, GC or UV analysis of the hexane layer revealed that no dienophile was left. To the magnetically stirred slurry of dienophilezeolite complex in n-hexane a solution of cyclopentadiene in n-hexane was added at once (2:1 molar ratio of diene:dienophile) and the mixture stirred for 4 h at room temperature. After filtration and washing with more n-hexane and small portions of diethyl ether, GC analysis of the filtrate revealed no product in the filtrate. The product was readily extracted into the ether layer by stirring the zeolite in diethyl ether overnight (mass balance ∼ 90%). The product was analyzed by GC (using 10 ft. OV-17 on Chromosorb column with cyclohexanone as internal standard) and NMR for endo:exo ratio and ee using a chiral shift reagent. The absolute configuration has not been determined.
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