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Updated: Jun 19, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Enantioselective enzymatic desymmetrization of highly functionalized meso tetrahydropyranyl diols
Mathieu Candy1, Gérard Audran, Hugues Bienaymé
1Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 CNRS UMR6263-équipe STeRéO Campus Saint-Jérôme, 13397 Marseille Cedex 20, France.
Abstract:
The enantioselective enzymatic desymmetrization of several highly substituted meso-tetrahydropyranyl diols is described. This transformation leads to valuable building blocks containing up to five stereogenic centers, which are revealed in a single step with both high yields and excellent enantiomeric excesses. Moreover, it was shown that this kind of building blocks could provide an easy access to both enantiomers of highly functionalized stereotetrads.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

