15384-61-9Relevant articles and documents
CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES FROM AMINOSUGAR N-OXIDES. ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED PYRROLIDINES
Chastanet, Jacqueline,Fathallah, Hassana,Negron, Guillermo,Roussi, Georges
, p. 1565 - 1572 (2007/10/02)
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 cycloaddition to stilbene are thus obtained with good asymmetric induction.The easy elimination of the chiral appendage as starting epoxides gives access to the enantiomerically enriched 3,4-diphenylpyrrolidines.