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Synthesis of enantioenriched azo compounds: organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes†

David Monge,*a   Silvia Daza,a   Pablo Bernal,b   Rosario Fernández*a  and  José M. Lassaletta*b  
Author affiliations

* Corresponding authors

a Departamento de Química Orgánica, Universidad de Sevilla, C/Prof. García González, 1, 41012 Sevilla, Spain
E-mail: dmonge@us.es, ffernan@us.es
Fax: +34 954624960
Tel: +34 954551518

b Instituto de Investigaciones Químicas CSIC-US, Américo Vespucio 49, E-41092 Sevilla, Spain
E-mail: jmlassa@iiq.csic.es
Fax: +34 954460565
Tel: +34 954489563

Abstract

The unprecedented diaza–ene reaction of formaldehyde N-tert-butyl hydrazone with nitroalkenes can be efficiently catalyzed by an axially chiral bis-thiourea to afford the corresponding diazenes in good to excellent yields (60–96%) and moderate enantioselectivities, up to 84 : 16 er; additional transformation of diazenes into their tautomeric hydrazones proved to be operationally simple and high-yielding, affording bifunctional compounds which represent useful intermediates for the synthesis of enantioenriched β-nitro-nitriles and derivatives thereof.

Graphical abstract: Synthesis of enantioenriched azo compounds: organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes

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Article information

https://doi.org/10.1039/C2OB26963E
Submitted
09 Oct 2012
Accepted
09 Nov 2012
First published
09 Nov 2012
Org. Biomol. Chem., 2013,11, 326-335
Article type
Paper
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Synthesis of enantioenriched azo compounds: organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes

D. Monge, S. Daza, P. Bernal, R. Fernández and J. M. Lassaletta, Org. Biomol. Chem., 2013, 11, 326
DOI: 10.1039/C2OB26963E

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