A New Twist on Amide Solvolysis

Authors

  • Prof. Jeffrey Aubé

    Corresponding author
    1. Department of Medicinal Chemistry, University of Kansas, Delbert M. Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, KS 66047-3761 (USA)
    • Department of Medicinal Chemistry, University of Kansas, Delbert M. Shankel Structural Biology Center, 2034 Becker Drive, Lawrence, KS 66047-3761 (USA)
    Search for more papers by this author

Abstract

original image

Planar but destabilized: Amides prepared from hindered amines and carbonyl compounds containing an electron-withdrawing substituent (EWG) have recently been shown to undergo solvolysis at greatly enhanced rates under neutral conditions. The key is increased access to a twisted amide conformation that undergoes a proton switch, ultimately leading to the observed products.

Ancillary