Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrones with (S)-(-)-4-Benzyl-N-methacryloyl-2-oxazolidinone

Abstract

The [3+2]-nitrone-mediated cycloaddition reaction of (S)-(-)-4-benzyl-N-methacryloyl-2-oxazolidinone has been applied to the synthesis of highly substituted isoxazolidines with controlled stereochemistry. The absolute configuration of the major diastereo­isomer derived from the reaction between N-(p-nitrobenzylidene)methylamine N-oxide and (S)-(-)-4-benzyl-N-methacryloyl-2-oxazolidinone has been deduced from the corresponding X-ray structure.

Key words

chiral auxiliary - nitrones - dipolar cycloaddition reaction - isoxazolidine - isoxazolidinone

References

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18

All compounds provided satisfactory spectral data that were consistent with the assigned structures.

20

Only one isomer was detectable by ¹H NMR studies on the crude isolate.

21

The enantiomeric excess (92%) was determined by chiral GC using a Supercot α-dex 225 column.