A Facile Synthesis of a Spironitrone
and a Study of Its Cycloaddition and Nucleophilic Addition
Reactions

Daryl Crimmins; Ivaylo Dimitrov; Patrick D. O’Connor; Vittorio Caprio; Margaret A. Brimble

doi:10.1055/s-0028-1083151

PAPER

A Facile Synthesis of a Spironitrone and a Study of Its Cycloaddition and Nucleophilic Addition Reactions

Daryl Crimmins, Ivaylo Dimitrov, Patrick D. O’Connor, Vittorio Caprio, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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Abstract

The synthesis of spironitrone 5 via microwave-assisted intramolecular alkylation of bromo oxime 10 is reported. The bromo oxime is prepared by alkylation of methyl cyclohexanecarboxylate with 1,4-dibromobutane followed by conversion of the methyl ester to an oxime. Spironitrone 5 undergoes facile 1,3-dipolar cycloaddition to a range of olefins to form a range of spirocyclic isoxazolidines. Nucleophilic addition of several Grignard reagents to spironitrone 5 provided access to a series of alkyl-substituted spirohydroxylamines.

Key words

1,3-dipolar cycloaddition - spironitrones - microwave - Grignard reagents

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Referenzen

References

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