Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols

Jake L. Stymiest, Viktor Bagutski, Rosalind M. French and Varinder K. Aggarwal ()
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Jake L. Stymiest: School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK
Viktor Bagutski: School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK
Rosalind M. French: School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK
Varinder K. Aggarwal: School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK

Nature, 2008, vol. 456, issue 7223, 778-782

Abstract: Tertiary alcohols on tap Chiral molecules, for which two mirror images that cannot be superposed onto each other exist, are common in nature as are cellular receptors able to distinguish between the two mirror images or enantiomers. Some types of chiral molecules can be readily synthesized enantioselectively, but one class — those containing quaternary stereogenic centres — remains a major challenge. Stymiest et al. now present a new method that converts secondary alcohols in their single mirror image form into tertiary alcohols. Either mirror image form of the tertiary alcohol can be made from the same starting material with very high levels of stereocontrol. A broad range of tertiary alcohols can easily be made by this method, with high levels of enantioselectivity.

Date: 2008
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DOI: 10.1038/nature07592

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