Tetrahedron

Some unusual reactivities in the SmI 2-mediated reductive coupling of acrylamides and acrylates with imides

RH Taaning, KB Lindsay, T Skrydstrup

Index: Taaning, Rolf H.; Lindsay, Karl B.; Skrydstrup, Troels Tetrahedron, 2009 , vol. 65, # 52 p. 10908 - 10916

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Citation Number: 6

Abstract

A serendipitous discovery of some intra-molecular enolate addition reactions following a SmI2-mediated reductive cross-coupling between imides and electron-deficient olefins leading to some novel compounds was investigated to determine the generality of the protocol and the possible mechanistic pathways involved. This provided a Z-selective synthesis of γ-ketoenediamides in good yields, albeit as of now the substrate scope ...