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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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Article information


Submitted
12 Jul 2013
Accepted
08 Oct 2013
First published
09 Oct 2013

Org. Biomol. Chem., 2013,11, 8247-8255
Article type
Paper

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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