Synfacts 2009(3): 0284-0284  
DOI: 10.1055/s-0028-1087778
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantiodivergent Synthesis of Tertiary Alcohols from Secondary Carbamates

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal*
University of Bristol, UK
Further Information

Publication History

Publication Date:
19 February 2009 (online)

Significance

This paper described the stereo­divergent synthesis of tertiary alcohols from chiral secondary carbamates through lithiation-borylation followed by subsequent oxidation. This methodology afforded a very broad range of tertiary alcohols in high yields and high enantioselectivities. Remarkably, either enantiomer of the tertiary alcohol could be obtained with high enantioselectivity from the same enantiomer of the secondary alcohol depending on whether a borane or boronic ­ester is used.