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

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

Key words

vinyl sulfone - cycloheptadienyl - cyclohexadienyl - bromination - pyridinium salt - Jacobsen epoxidation

References

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  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.