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Synthesis 1995; 1995(9): 1171-1178
DOI: 10.1055/s-1995-4060
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Intramolecular 1,3-Dipolar Cycloaddition of Transient Enantiomerically Pure Oxaalkenyl Nitrones

Hans Günter Aurich* , Frank Biesemeier
  • *Fachbereich Chemie, University of Marburg, D-35032 Marburg, Germany
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Publication Date:
31 December 2000 (online)

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A variety of enantiomerically pure α-hydroxy esters were converted into enantiomerically pure 3,7-dioxa-2-azabicyclo[3.3.0]octanes 7 by the following reaction sequence. Allylation of the hydroxy group was followed by reduction of the ester group. The resulting aldehyde was treated with an N-alkylhydroxylamine to give an oxaalkenyl nitrone 6 which underwent spontaneously an intramolecular 1,3-dipolar cycloaddition affording 7. Opening of the isoxazolidine ring of 7 by various reductive methods yielded the highly substituted tetrahydrofuran derivatives 11.

diastereoselective intramolecular cycloaddition - 3,7-dioxa-2-azabicyclo[3.3.0]octanes - asymmetric induction - 3-alkylamino-4-hydroxymethyltetrahydrofurans - α-allyloxy esters