REGIOSELECTIVITY IN DEPROTONATION OF IMINES DERIVED FROM 3-PENTANONE
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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.