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Synfacts 2009(3): 0284-0284
DOI: 10.1055/s-0028-1087778
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
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.