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

Rebecca Newton; G. Paul Savage

doi:10.1071/ch08111

journal article Jun 19, 2008

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

Rebecca Newton G. Paul Savage

Australian Journal of Chemistry Vol. 61 No. 6 pp. 432-437 · CSIRO Publishing

View at Publisher Save 10.1071/ch08111

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.

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Details

Published: Jun 19, 2008
Vol/Issue: 61(6)
Pages: 432-437
License: View

Authors

R

Rebecca Newton

ACSIRO Molecular and Health Technologies, Private Bag 10, Clayton South MDC, VIC 3169, Australia.

G

G. Paul Savage

ACSIRO Molecular and Health Technologies, Private Bag 10, Clayton South MDC, VIC 3169, Australia.; BCorresponding author. Email: paul.savage@csiro.au

Cite This Article

Rebecca Newton, G. Paul Savage (2008). Regioselective 1,3-Dipolar Cycloaddition Reactions of 4-Methylene-2-oxazolidinones with Benzonitrile Oxide. Australian Journal of Chemistry, 61(6), 432-437. https://doi.org/10.1071/ch08111

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

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