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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: rss1805louisiana.edu

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

DOI: 10.1021/jo301266f (free Supporting Information)


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Abstract

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.

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proposed reaction pathway



Key Words

allylic amines, arylamines, Ene Reaction


ID: J42-Y2012-2730