ChemInform Abstract: The Selective Generation of Regioisomeric Tetrahydropyridine N-Oxides

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.