Single diastereomers of polyhydroxylated 9-oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of omega-unsaturated nitrones |
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Authors: | Padar Petra Bokros Attila Paragi Gabor Forgó Péter Kele Zoltan Howarth Nicola M Kovacs Lajos |
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Institution: | Department of Medicinal Chemistry, University of Szeged, H-6720, Hungary. |
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Abstract: | 8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and omega-unsaturated hydroxylamine 7 derived from methyl alpha-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo4.2.1]nonane was afforded in a similar manner, from methyl D-galactopyranoside and methyl glyoxylate, as a 3:1 mixture of diastereoisomers 15 and 16. When conducted in achiral ionic liquid 17 this ratio increased to 8:1, and in chiral ionic liquid 18, compound 15 was formed exclusively. |
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