Journal
ORGANIC LETTERS
Volume 5, Issue 21, Pages 3875-3878Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol035423v
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[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.
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