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Digitale Medien

Synthese homochiraler 3-Oxa-2,7-diazabicyclo[3.3.0]octane aus Aminosäuren durch intramolekulare 1,3-dipolare Cycloaddition von Nitronen (1993)

Aurich, Hans Günter ; Frenzen, Gerlinde ; Gentes, Christian

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 787-795

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Details

ISSN: 0009-2940

Schlagwort(e): Heterobicyclo[3.3.0]octanes, homochiral ; Amino acids ; Nitrones ; Cycloadditions, diastereoselective, intramolecular ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Synthesis of Homochiral 3-Oxa-2,7-diazabicyclo[3.3.0]octanes from Amino Acids by Intramolecular 1,3-Dipolar Cycloaddition of NitronesN1-Allylamino alcohols 9 were prepared from amino acids by various methods. Swern oxidation of 9 afforded aldehydes 11. By reaction of 11 with N1-alkylhydroxylamines nitrone intermediates 4 were formed which spontaneously underwent an intramolecular 1,3-dipolar cycloaddition to yield the bicyclic compounds 6. The cycloaddition proceeds diastereoselectively furnishing homochiral compounds 6 from homochiral starting materials. The structure of 6aA was confirmed by X-ray structural analysis.

Zusätzliches Material: 2 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/cber.19931260333

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