We will report two methods to effect an enantioselective tandem aldol/epoxidation reaction. (Figure 1)  In this reaction three new stereocenters are generated.  With each method the reaction is highly diastereoselective.  Method a achieves an enantiomeric ratio of about 4:1 while method b provides an enantiomeric ratio of up to 34:1.  Mechanistic details of this reaction will be reported as well as preliminary toxicity studies using the Brine Shrimp Lethality Assay.

Enantioselective aldol/epoxidation

245th National Meeting (2013)

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