Enantioselective Enzymatic Desymmetrization of Highly Functionalized Meso Tetrahydropyranyl Diols

Mathieu Candy (1) , Gérard Audran (1) , Hugues Bienaymé , Cyril Bressy (1) , Jean-Marc Pons (1)

1 STeRéO

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.

Mots clés: Desymmetrization; Meso diols; Tetrahydropyran; Enzymes; Ring-Opening

Domaines: Chimie organique

Mathieu Candy, Gérard Audran, Hugues Bienaymé, Cyril Bressy, Jean-Marc Pons. Enantioselective Enzymatic Desymmetrization of Highly Functionalized Meso Tetrahydropyranyl Diols. Organic Letters, 2009, 11, pp.4950-4953. ⟨10.1021/ol902107g⟩. ⟨hal-00678921⟩