Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d8 in the absence and in the presence of lithium halides were studied by 6Li and 15N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry