Enantioselective Synthesis of Protected α-Hydroxy AldehydesviaAlkylation of Metalated Chiral Hydrazones

Abstract
α-Hydroxy aldehydes 4 bearing various protecting groups, such as the tert-butyldiphenylsilyl (TBDPS), the benzyloxymethyl (BOM) and the benzyl group, are prepared in high enantiomeric excess by azaenolate alkylation of protected α-hydroxy acetaldehyde hydrazones 2, novel synthetic equivalents of the α-hydroxy acetaldehyde d2-synthon.

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