Claisen Rearrangement of Carbohydrate-Derived Precursors Towards Highly Functionalized Cyclooctenones with L-xylo, D-arabino and L-lyxo Configuration and Their Diastereoselective Transformations

Claisen Rearrangement of Carbohydrate-Derived Precursors Towards Highly Functionalized Cyclooctenones with L-xylo, D-arabino and L-lyxo Configuration and Their Diastereoselective Transformations

D‐Glucose and D‐mannose have been transformed into precursors incorporating allyl vinyl ether substructures. Both thermally and catalytically, these cyclic allyl vinyl ethers could be converted into the corresponding Claisen rearrangement products. The conformations of these enantiopure 5‐cycloocten...

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Veröffentlicht in:European Journal of Organic Chemistry 2006-10, Vol.2006 (19), p.4451-4462
Hauptverfasser: Jürs, Stefan, Werschkun, Barbara, Thiem, Joachim
Format: Artikel
Sprache:eng
Schlagworte:
Allyl vinyl ethers
Carbocycles
Carbohydrates
Claisen rearrangement
Mimetics
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Zusammenfassung:D‐Glucose and D‐mannose have been transformed into precursors incorporating allyl vinyl ether substructures. Both thermally and catalytically, these cyclic allyl vinyl ethers could be converted into the corresponding Claisen rearrangement products. The conformations of these enantiopure 5‐cyclooctenones were studied by NMR spectroscopy and X‐ray crystallography. They proved to be versatile substrates for highly stereo‐ and regioselective modifications. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600455