Jump to main content
Jump to site search

Issue 2, 2013
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
09 Oct 2012
Accepted
09 Nov 2012
First published
09 Nov 2012

Org. Biomol. Chem., 2013,11, 326-335
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements