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Synlett 2000; 2000(9): 1228-1240
DOI: 10.1055/s-2000-7122
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Formaldehyde N,N-Dialkylhydrazones as C-1 Building-blocks in Asymmetric Synthesis

José M. Lassaletta* , Rosario Fernández
  • *Instituto de Investigaciones Química (CSIC-USe), c/ Amerigo Vespuccio s/n, Isla de la Cartuja, E-41092 Seville, Spain
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Publication Date:
31 December 2000 (online)

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The aza-enamine character of formaldehyde N,N-dialkylhydrazones can be exploited for their use as d1-synthons in the addition reaction to a variety of electrophilic substrates, including Michael acceptors and carbonyl compounds. Using readily available proline-derived chiral forms of these reagents, a variety of bi-functional adducts can be obtained with high optical purity. The availability of racemization-free cleavage methods for the transformation of these hydrazones into the corresponding aldehydes and nitriles makes these reagents to appear as a new class of chiral, neutral formyl anion and cyanide equivalents.

asymmetric synthesis - hydrazones - nucleophilic addition - d1 synthons - Umpolung