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Synlett 1991; 1991(1): 47-48
DOI: 10.1055/s-1991-20624
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The Selective Generation of Regioisomeric Tetrahydropyridine N-Oxides

Andrew B. Holmes* , Andrew B. Hughes, Adrian L. Smith
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, England
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Publication Date:
07 March 2002 (online)

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Whereas the oxidative cleavage of bicyclic isoxazolidines 5 (2-phenylperhydroisoxazolo[2,3-a]pyridine) and 9 (6-(2-benzyloxyethyl)- 8 -(3-phenylsulfonylpropyl)-7 -oxa-1-azabicyclo-[3.2.1]octane) with magnesium monoperoxyphthalate (MMPP) significantly favours the formation of the more substituted tetrahydropyridine N-oxides, 3-chloroperoxybenzoic acid (mCPBA) is shown to favour the less substituted nitrone 10 in reaction with the more substituted isoxazolidine 9.