Some unusual reactivities in the SmI2-mediated reductive coupling of acrylamides and acrylates with imides

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  • iNano-School
  • Interdisciplinary Nanoscience Center
  • Department of Chemistry
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 [gamma]-ketoenediamides in good yields, albeit as of now the substrate scope remains limited. It was also shown that the seemingly similar acrylate substrates can behave differently compared to the corresponding acrylamides in their SmI2-mediated reductive cross-coupling reaction with imides, and it was argued that these diverging reactivities are dominated by the ability of the acrylates to coordinate the samarium metal centre.
Original languageEnglish
JournalTetrahedron
Volume65
Issue52
Pages (from-to)10908-10916
Number of pages9
ISSN0040-4020
Publication statusPublished - 2009

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