Intramolecular cycloaddition reactions of silyl nitronate tethered to vinylsilyl group: 2-nitroalkanols as precursors for amino polyols

[GRAPHICS] A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et3N in CH3CN at 0 degreesC to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2] cycloaddition reaction. Some examples for transforming the cycloadducts to amino polyols are also presented.