Journal of the Chemical Society. Perkin transactions I p. 2787 - 2796 (1987)
Update date:2022-08-11
Topics:
Atkinson, Robert S.
Tughan, Gary
Oxidation of the optically active 1-aminobenzimidazoles (5)-(7) with lead tetra-acetate in the presence of various prochiral alkenes yields mixtuters of the diastereoisomeric aziridines with little asymmetric induction (Table).Oxidation of the racemic 1-amino-2-(1,2,2-trimethylpropyl)-1H-benzimidazole (12) in the presence of α-methylene-γ-butyrolactone (1) yields the stereoisomeric aziridines (16) in a 5.5:1 ratio, and oxidation in the presence of γ,γ-dimethyl-α-methylene-γ-butyrolactone (18) gives the aziridine (19) stereospecifically.The stereochemistry of (19) was determined by X-ray crystallography.A rationalisation for the stereospecificity of addition of the intermediate N-nitrene, produced by oxidation of (12) to the lactone (18), is given in terms of competitive reaction via two different transition states both of which lead to the same sense of chiral induction (Scheme 5).Significant asymmetric introduction is also found in the addition of the nitrene derived from oxidation of (12) to (E)-but-2-ene (5.2:1 ratio of stereoisomers) and styrene (5.6:1 ratio of stereoisomers).
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