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Enantiomerenreine 3,7-Dioxa-2-azabicylo[3.3.0]octane durch intramolekulare 1,3-dipolare Cycloaddition von Nitronen

✍ Scribed by Güinter Aurich, Hans ;Biesemeie, Frank ;Boutahar, Mostafa

Publisher
Wiley (John Wiley & Sons)
Year
1991
Tongue
English
Weight
670 KB
Volume
124
Category
Article
ISSN
0009-2940

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✦ Synopsis

Nitrones / Cycloaddition, intramolecular / Asymmetric induction / Heteroanaloga of bicyclo[3.3.0]octanes, enantiomerically pure / Tetrahydrofuran derivatives, y-amino alcohols Enantiomerically Pure 3,?-Dioxa-2-azabicyclo[3.3.0]octanes by Intramolecular 1,3-Dipolar Cycloaddition of Nitrones

Starting with chiral non-racemic esters of lactic acid 7 and mandelic acid 8, respectively, chiral nitrones 4 have been prepared. They spontaneously undergo an intramolecular cycloaddition which proceeds with asymmetric induction by the chiral center yielding exclusively the bicyclic compounds 5 in enantiomerically pure form. Reductive opening of the isoxazolidine ring affords tetrahydrofuran derivatives 13 with an y-amino alcohol group. Reaction of 13 with (-)-camphanoyl chloride gives the esters 14. Their 'H-NMR spectra reveal a diastereomeric purity of at least 98%.

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