Tetrahedron

Synthesis of enamides from aldehydes and amides

A Bayer, ME Maier

Index: Bayer, Alexander; Maier, Martin E. Tetrahedron, 2004 , vol. 60, # 31 p. 6665 - 6677

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Citation Number: 64

Abstract

A range of double unsaturated amides (,, and), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac2O and pyridine affected clean conversion to the corresponding enamides, such as,, and. Alternatively, N, S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less ...