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Issue 47, 2013
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Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones

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Abstract

The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields (50–96%) and moderate to good enantioselectivities, up to 86% ee. Further transformations of the nitrile functionality allow access to useful protected hydrazino acids and imidazolidinones. Interestingly, some of the hydrazino nitriles and their derivatives could be recrystallized in high recovery, yielding essentially pure enantiomers.

Graphical abstract: Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones

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Publication details

The article was received on 12 Jul 2013, accepted on 08 Oct 2013 and first published on 09 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41437J
Citation: Org. Biomol. Chem., 2013,11, 8247-8255
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    Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones

    A. Martínez-Muñoz, D. Monge, E. Martín-Zamora, E. Marqués-López, E. Álvarez, R. Fernández and J. M. Lassaletta, Org. Biomol. Chem., 2013, 11, 8247
    DOI: 10.1039/C3OB41437J

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