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Cobalt-Catalyzed Regioselective Synthesis of Pyrrolidinone Derivatives by Reductive Coupling of Nitriles and Acrylamides

Ying-Chieh Wong, Kanniyappan Parthasarathy and Chien-Hong Cheng*

*Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan, Email: chchengmx.nthu.edu.tw

Y.-C. Wong, K. Parthsarathy, C.-H. Cheng, J. Am. Chem. Soc., 2009, 131, 18252-18253.

DOI: 10.1021/ja9088296 (free Supporting Information)


Abstract

A convenient and highly regioselective method allows the synthesis of 5-methylenepyrrolidinone derivatives from various nitriles and acrylamides via a cobalt-catalyzed reductive coupling reaction. A possible mechanism involves the formation of a cobaltaazacyclopentene intermediate from nitrile and acrylamide, protonation, keto-amide cyclization, and dehydration.

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proposed mechanism



Key Words

γ-Lactams, Zinc


ID: J48-Y2009-3680