Synlett 2008(15): 2386-2387  
DOI: 10.1055/s-2008-1067139
© Georg Thieme Verlag Stuttgart ˙ New York

N-Benzyl-2,3-O-isopropylidene-d-glyceraldehyde Nitrone

Gabriel Podolan*
Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237 Bratislava, Slovak Republic
Further Information

Publication History

Publication Date:
02 July 2008 (online)


N-Benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (1; Scheme  [¹] ) is a highly flexible compound that can be used as reagent in a number of addition reactions, [3+2] cycloadditions, and the new [3+3] cyclization leading to chiral nitrogen-containing acyclic and cyclic products. The enantiopure nitrone can be prepared by a very effective route from the readily available d-mannitol. Starting with a regioselective ketalization, oxidative diol cleavage of the resulting glycol results in the d-glyceraldehyde precursor. [¹] Treatment of this aldehyde with N-benzylhydroxylamine in the presence of MgSO4 gives nitrone 1 in excellent yield. [²]

Scheme 1


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