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

Organic & Biomolecular Chemistry Pub Date: 2012-11-09 DOI: 10.1039/C2OB26963E

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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