Organic Chemistry Portal



Direct Synthesis of β-Alkyl N-Aryl Aza Baylis-Hillman Adducts via Nitroso-Ene Reaction

Siva Murru, August A. Gallo and Radhey S. Srivastava*

*Department of Chemistry, University of Louisiana at Lafayette, Lafayette, Louisiana 70504, United States, Email:

S. Murru, A. A. Gallo, R. S. Srivastava, J. Org. Chem., 2012, 77, 7119-7123.

DOI: 10.1021/jo301266f

see article for more reactions


A direct Fe-catalyzed synthesis of β-alkyl N-aryl aza Baylis-Hillman (ABH) adducts involves the formation of a C-N bond via a nitroso-ene reaction. This is a simple, fast, and best alternate method to overcome the substrate scope limitations of the ABH reaction. Various arylhydroxylamines reacted with esters, aldehydes, ketone, and nitriles to yield the corresponding products in good yields.

see article for more examples

proposed reaction pathway

Key Words

allylic amines, arylamines, Ene Reaction

ID: J42-Y2012-2730