The Journal of Organic Chemistry

New synthesis of nitrogen heterocycles through amide-directed hydrocarbonylation of alkenamides catalyzed by rhodium complexes

I Ojima, A Korda, WR Shay

Index: Ojima, Iwao; Korda, Anna; Shay, William R. Journal of Organic Chemistry, 1991 , vol. 56, # 6 p. 2024 - 2030

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Citation Number: 60

Abstract

Amide-directed hydrocarbonylation of 3-butenamide (1) catalyzed by rhodium complexes such as RhCl (PPha) 3, RhCl (CO)(PPh3) 2, HRh (CO)(PPh,),, and Rh,(C0) 12 gives a mixture of 3, 4-dihydro-2-pyridone (2), 4-methyl-3-pyrrolin-2-one (31, and a unique heterodimer, 6-(4methyl-2-oxo-3-pyrrolin-l-yl)-2-piperidone (4). Dihydropyridone (2) is obtained in 88% yield with 98% selectivity by using HRh (CO)(PPh),-dppb (2 equiv) ...