New synthesis of Evans chiral oxazolidinones by using Sharpless AA reaction

Abstract

Optically pure new Evans auxiliary analogs, (4R)- and (4S )-4-(2-naphthyl)oxazolidin-2-one, have been synthesized by using the Sharpless catalytic asymmetric aminohydroxylation reaction (Sharpless AA). The concise two-step synthesis involves a unique solution-to-solid Sharpless AA process and new neat cyclization conditions.

References

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20. The neat cyclization can be conducted by using a catalytic amount of K₂CO₃(10 mol%) and gave a lower yield of 82%.
21. 99% ee indicates that only one enantiomer was observed in HPLC analysis.