Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones

Petra Pádár, Attila Bokros, Gábor Paragi, Péter Forgó, Zoltán Kele, Nicola M. Howarth, Lajos Kovács

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22 Citations (Scopus)

Abstract

8-Benzyloxymethyl-3,4,5-tribenzoyloxy-9-oxa-1-azabicyclo[4.2.1]nonane has been prepared as the single diastereoisomer 8 from an intramolecular 1,3-dipolar cycloaddition involving 2-(benzyloxy)acetaldehyde and ?-unsaturated hydroxylamine 7 derived from methyl a-D-glucopyranoside. The analogous 8-methoxycarbonyl 9-oxa-1-azabicyclo[4.2.1]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. © 2006 American Chemical Society.

Original languageEnglish
Pages (from-to)8669-8672
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number22
DOIs
Publication statusPublished - 27 Oct 2006

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