Synfacts 2010(9): 1041-1041  
DOI: 10.1055/s-0030-1257951
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Addressing Challenges in the Stereospecific Lithiation-Borylation of Carbamates

Contributor(s): Mark Lautens, David A. Candito
V. Bagutski, R. M. French, V. K. Aggarwal*
University of Bristol, UK
Further Information

Publication History

Publication Date:
23 August 2010 (online)

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.