Synthesis p. 3319 - 3325 (2008)
Update date:2022-08-04
Topics:
Crimmins, Daryl
Dimitrov, Ivaylo
O'Connor, Patrick D.
Caprio, Vittorio
Brimble, Margaret A.
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.
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(2009)
