Regioselective 1,3-Dipolar Cycloaddition Reactions of 4-Methylene-2-oxazolidinones with Benzonitrile Oxide

Rebecca Newton; G. Paul Savage

doi:10.1071/CH08111

RESEARCH ARTICLE

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Regioselective 1,3-Dipolar Cycloaddition Reactions of 4-Methylene-2-oxazolidinones with Benzonitrile Oxide

Rebecca Newton ^A and G. Paul Savage ^A ^B

+ Author Affiliations

- Author Affiliations

^A CSIRO Molecular and Health Technologies, Private Bag 10, Clayton South MDC, VIC 3169, Australia.

^B Corresponding author. Email: paul.savage@csiro.au

Australian Journal of Chemistry 61(6) 432-437 https://doi.org/10.1071/CH08111
Submitted: 19 March 2008 Accepted: 5 May 2008 Published: 19 June 2008

Abstract

Substituted 4-methylene-2-oxazolidinones were prepared in two steps by cyclizing O-propargyl carbamates, which in turn were prepared from propargyl alcohols and phenyl isocyanate. The 4-methylene-2-oxazolidinones underwent a 1,3-dipolar cycloaddition reaction with benzonitrile oxide to give the corresponding spiro heterocycles. Where the substitution pattern on the oxazolidinone engendered facial asymmetry, the cycloadditon reaction proceeded with 5:1 selectivity for the less hindered face of the dipolarophile.

Acknowledgement

The authors wish to thank Craig Forsyth for the X-ray structure determinations, and Karen Jarvis for technical assistance.

References

Regioselective 1,3-Dipolar Cycloaddition Reactions of 4-Methylene-2-oxazolidinones with Benzonitrile Oxide

Abstract

Acknowledgement

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