• From left: Dr. B. W. Greatrex, E. T. Ledingham, Dr. M. K. Taylor (University of New England, Australia)

    From left: Dr. B. W. Greatrex, E. T. Ledingham, Dr. M. K. Taylor (University of New England, Australia)

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Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives

Ben Greatrex presents the stereoselective cyclopropanation of (–)-levoglucosenone derivatives.

Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides: E. T. Ledingham, C. J. Merritt, C. J. Sumby, M. K. Taylor, Ben W. Greatrex
Synthesis 2017, 49, 2652–2662

(–)-Levoglucosenone is a readily available, versatile and highly functionalized bicyclic chiral building block that can be produced from abundant lignocelluloses in a single synthetic step. It therefore represents a very useful and convenient starting material for the preparation of chiral non-racemic complex compounds. A new use of (–)-levoglucosenone for the stereoselective synthesis of cyclopropanes has been reported by Dr. Ben W. Greatrex and co-workers from the University of New England (Amidale, Australia) in a recent issue of Synthesis.

  • Stereoselective cyclopropanation of (–)-levoglucosenone derivatives

    Stereoselective cyclopropanation of (–)-levoglucosenone derivatives

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Dr. Greatrex said: “The mild conditions are highly selective for cyclopropanation over competing epoxidation, and applied to levoglucosenone, have enabled the synthesis of highly substituted cyclopropanes from this useful biomass derivative.” 

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