Diastereoselective arylithium addition to an [alpha]-trifluoromethyl imine. Practical synthesis of a potent cathepsin k inhibitor

The discovery of a highly diastereoselevtive addition of 4-bromophenyllithium to imine derived form commercially available (S)-leucinol allowed the rapid development of a scaleable synthesis of a potent and selective cathepsin K inhibitor. The molecules capable of selectively inhibiting cathepsin K might serve as useful therapeutic agents against disease such as osteoporosis and other bone disorders involving excessive bone loss.