The barriers to enantiomerization of N-trimethylallyl-2-lithiopyrrolidine have been measured in the presence of sparteine, 1, N,N'-diisopropylbispidine, 2, and diaminoalkoxide 3. We have additionally demonstrated a rare example of a catalytic dynamic resolution using either of two ligands, achieving enantiomer ratios of up to 93:7.