194862-75-4Relevant academic research and scientific papers
Two different pathways of stereoinformation transfer: Asymmetric substitutions in the (-)-sparteine mediated reactions of laterally lithiated N,N-diisopropyl-o-ethylbenzamide and N-pivaloyl-o-ethylaniline
Thayumanavan,Basu, Amit,Beak, Peter
, p. 8209 - 8216 (2007/10/03)
Highly enantioenriched substitution products can be obtained by the (-)-sparteine mediated lithiation-substitution reactions of the laterally lithiated intermediates 3·1 and 14·1 derived from the amides 2 and 13. Either enantiomer of the products can be obtained with high enantioenrichment using (-)-sparteine as the ligand by appropriate choice of the protocol. The enantiodetermining step in both sequences occurs after deprotonation. Enantioenrichment in the sequence with 3·1 arises from a dynamic kinetic resolution, whereas enantioenrichment in the sequence with 14·1 arises from a dynamic thermodynamic resolution.
