100. “The Photohydration of N-Glycosylpyridinium Salts and of Related Pyridinium N,O-Acetals”
     Glarner, F.; Acar, B.; Etter, I.; Damiano, T.; Acar, E. A.; Bernardinelli, G.; Burger, U.
     Tetrahedron 2000, 56, 4311-4316.

The photolysis of N-MEM-pyridinium chloride (1e) in alkaline H₂O gave N-MEM-6-azabicyclo[3.1.0]hexenol (2e). With benzoic acid in CHCl₃, this bridged aziridine gave a complex aminal 7 reminiscent by its C₂ symmetry of Tröger's base. Photolysis of α-D-glucopyranosyl pyridinium chloride (α-12) gave a 1:1 mixture of the corresponding α-D-glucopyranosyl aziridines (α-13/α-14), which were separated, after peracetylation, by crystallisation. The absolute configuration of one of the bridged aziridines (α-16) was established by X-ray analysis.

DOI : 10.1016/S0040-4020(00)00357-4 

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