Multigram Synthesis of Diastereomerically Pure Tetrahydrofuran-diols

Sabrina Göhler; Stefanie Roth; Huan Cheng; Hülya Göksel; Alexander Rupp; Lars O. Haustedt; Christian B. W. Stark

doi:10.1055/s-2007-983797

PSP

Multigram Synthesis of Diastereomerically Pure Tetrahydrofuran-diols

Sabrina Göhler^a, Stefanie Roth^a, Huan Cheng^a, Hülya Göksel^a, Alexander Rupp^a, Lars O. Haustedt^b, Christian B. W. Stark*^a
^a Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
Fax: +49(30)83855367; e-Mail: stark@chemie.fu-berlin.de;
^b AnalytiCon Discovery GmbH, Hermannswerder Haus 17, 14473 Potsdam, Germany

Abstract

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Abstract

A highly efficient protocol for the large-scale oxidative cyclization of 1,5-dienes is described. This convenient ruthenium(VIII)-catalyzed (0.2 mol%) cyclization reaction allows the preparation of cis-2,5-disubstituted tetrahydrofurans in high yields (up to 92%) and excellent diastereomeric ratio (>95:5 dr). This simple and reliable method is insensitive to moisture and air and can, therefore, be carried out in an open reaction vessel.

Key words

ruthenium - oxidation - cyclization - heterocycle - diastereoselectivity

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References

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