Addressing Challenges in the Stereospecific Lithiation-Borylation of Carbamates

Significance

The enantioselective synthesis of chiral tertiary alcohols remains a challenge in organic synthesis. The authors have previously developed an approach based on the lithiation of chiral secondary carbamates and their subsequent reaction with organoboron reagents (V. K. Aggarwal and co-workers Nature 2008, 456, 778). In the present report the authors address factors which are important to the enantio­selectivity of the process and provide solutions to overcome the poor selectivity observed with challenging substrates.