Regioselectivity in deprotonation of imines derived from 3-pentanone Academic Article uri icon


  • Regioselectivity in deprotonation of (Z)-tertbutyl, (Z)-cyclohexyl, (Z)-benzyl, and (Z)-phenyl ketimines of 3-pentanone has been shown to be generally low and variable. Deprotonation of 13CH3-labeled Z ketimines with either lithium diisopropylamide or lithium diethylamide in THF and methylation at -78 °C was used to determine regiochemistry. Syn/anti deprotonation ratios varied from 74/26 to 22/78 with different ketimines and different bases. © 1981, American Chemical Society. All rights reserved.

author list (cited authors)

  • Smith, J. K., Bergbreiter, D. E., & Newcomb, M.

citation count

  • 8

publication date

  • July 1981