177410-59-2Relevant academic research and scientific papers
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.
Stereoselective synthesis of oxazolidines from 2-amino-2-deoxy-D-allose derivatives and their reactivity with nucleophiles
Vega-Perez, Jose M.,Vega, Margarita,Blanco, Eugenia,Iglesias-Guerra, Fernando
, p. 135 - 147 (2007/10/03)
The use of 2-amino-2-deoxy-D-allose in the synthesis of oxazolidines is described. The reaction takes place with total stereoselectivity in the preparation of both simple oxazolidines (from aldehydes as reagent) and bicyclic oxazolidines (from chlorocarbonyl compounds and keto-acids as reagents). The reactivity of the obtained oxazolidines with hydride and alkylmagnesium chlorides is also described.
