195006-97-4Relevant articles and documents
Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-D-allose as chiral auxiliaries
Vega-Perez, Jose M.,Vega, Margarita,Blanco, Eugenia,Iglesias-Guerra, Fernando
, p. 3189 - 3203 (2007/10/03)
The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding α,β-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the oxirane moiety from the chiral auxiliary, which was also recovered.