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Inne
Synthesis of sugar-derived 2´-and 3´-substituted furans and their application in Diels-Alder reactions.
Autorzy
Rok wydania
2001
Czasopismo
European Journal of Organic Chemistry
Strony
2955-2964
DOI
10.1002/1099-0690(200108)2001:15<2955::AID-EJOC2955>3.0.CO;2-0
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A convenient synthesis of 2′- and 3′-furyl sugars in which the furan and the sugar parts are directly connected is presented. The key step comprises HF·py-induced cyclization of α,β-unsaturated carbonyl compounds (ketones or aldehydes) possessing terminal hydroxymethylene groups protected as TBDPS ethers. Treatment of such furan derivatives with N-phenylmaleimide under high-pressure conditions (11 kbar) produces the corresponding [4+2] adducts, with the endo forms predominating. At p = 1 atm and T = 20 °C, however, the exo isomers are formed as the main products. The [4+2] adducts undergo retro Diels−Alder reactions at elevated temperatures at atmospheric pressure.
Adres publiczny
https://doi.org/10.1002/1099-0690(200108)2001:15<2955::AID-EJOC2955>3.0.CO;2-0