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Paper | Regular issue | Vol 34, No. 8, 1992, pp.1565-1572
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6052
[3+2] Cycloaddition of Chiral Azomethine Ylides from Aminosugar N-Oxides. Enantioselective Synthesis of 3,4-Disubstituted Pyrrolidines

Jacqueline Chastanet, Hassana Fathallah, Guillermo Negron, and Georges Roussi*

*Institut de Chimie des Substances Naturelles, C.N.R.S., 91198 Gif-sur-Yvette, France

Abstract

The base deprotonation method, applied to amino-sugar N-oxides prepared from methyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranoside (8) and methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (9), allows the easy generation of complex and very reactive sugar azomethine ylides. Fair yields of the major diastereomeric pyrrolidines resulting from [3+2] cycloaddition to stilbene are thus obtained with good asymmetric induction. The easy climination of the chiral appendage as starting epoxides gives access to the enantiomerically enriched 3,4-diphenylpyrrolidines.