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Synlett 1994; 1994(10): 792-794
DOI: 10.1055/s-1994-23007
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Enantioselective Synthesis of Protected α-Hydroxy Aldehydes via Alkylation of Metalated Chiral Hydrazones

Dieter Enders* , Ulrich Reinhold
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
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Publication History

Publication Date:
22 March 2002 (online)

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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.