914451-11-9Relevant articles and documents
Single diastereomers of polyhydroxylated 9-Oxa-1-azabicyclo[4.2.1]nonanes from intramolecular 1,3-dipolar cycloaddition of ω-unsaturated nitrones
Padar, Petra,Bokros, Attila,Paragi, Gabor,Forgo, Peter,Kele, Zoltan,Howarth, Nicola M.,Kovacs, Lajos
, p. 8669 - 8672 (2007/10/03)
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 ω-unsaturated hydroxylamine 7 derived from methyl α-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.