The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural (2£,3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1,2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.
All Science Journal Classification (ASJC) codes
- General Chemistry
- Drug Discovery