Synthesis 2004(11): 1895-1900  
DOI: 10.1055/s-2004-822318
PSP
© Georg Thieme Verlag Stuttgart · New York

Improved and Environmentally Friendly Large-Scale Preparation of Cyclohexadienyl-, Cycloheptadienyl Sulfone and Enantiopure Epoxy Cycloheptyl Sulfones

Taesik Park, Eduardo Torres, Philip L. Fuchs*
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA
e-Mail: [email protected];
Further Information

Publication History

Received 28 January 2004
Publication Date:
30 March 2004 (online)

Abstract

Kilogram-scale amounts of cycloheptadienyl phenylsulfone and cyclohexadienyl phenylsulfone were prepared by one operation in 5 stages with over 50% yield and requiring no purification. A practical and efficient method for the Jacobsen asymmetric epoxidation of 1,3-cycloheptadienyl sulfone is described. The reported method is suitable for large-scale synthesis, does not use halogenated solvents nor does it require chromatography

    References

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  • 6

    Polyaniline-sulfuric acid salt gave a similar result to Montmorillonite KSF:

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9

Prepared from Aliquat 336 (Aldrich) according to Noyori’s procedure. [8]

10

Based on prices from Aldrich catalog, including reagents necessary for purification.