Regioselective palladium-catalysed amination of 4-chloroacetoxyalk-2-enoic esters: synthesis of pyrrol-2 (5 H)-ones (4-but-2-enelactams)

R Tanikaga, J Takeuchi, M Takyu, A Kaji

Index: Tanikaga, Rikuhei; Takeuchi, Jun; Takyu, Masayuki; Kaji, Aritsune Journal of the Chemical Society, Chemical Communications, 1987 , # 5 p. 386 - 387

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Abstract

Palladium(0)-catalysed reactions of 4-chloroacetoxyal k-2-enoic esters with amines selectively give 4-aminoalk-2-enoic esters, which are readily converted into pyrrol-2(5H)-ones (4-but-2-enelactams ). ... One of the most synthetically useful reactions involving organopalladium intermediates is the nucleophilic substitu- tion reaction of n-allylic Pd complexes with carbon, nitrogen, and oxygen nucleophiles. 1-3 Pdo-catalysed exchanges of allylic hydroxy compounds ,4,5 acetates ...