Journal of Organic Chemistry p. 3157 - 3158 (1981)
Update date:2022-08-04
Topics:
Smith, Kirk J.
Bergbreiter, David E.
Newcomb, Martin
Regioselectivity in deprotonation of (Z)-tert-butyl,(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 deg C was used to determine regiochemistry.Syn/anti deprotonation ratios varied from 74/26 to 22/78 with different ketimines and different bases.
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Doi:10.1021/acs.joc.5b02248
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(1981)
