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The amounts of carboxylic acid 5 generated in the α-oxyamination of an aldehyde and the tandem reaction of an alcohol under different reaction conditions are described in the supplementary information When (5R)-(+)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride (Aldrich 663069) was used instead of peptide catalyst 1, 3a was obtained in 28% yield and 66% ee For a review, see
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The resin catalyst was filtered off and washed after each cycle of the reuse. Gravimetric analysis of the dried resin indicated that 0 to 80% of copper-bipyridine complex remained inside the resin. The fairly broad range in the amount of the residual copper complex might be due to the difference in washing conditions. In the reuse of the peptide catalyst, the copper salt and bipyridine were added in order to ensure the reproducibility regardless of the way of washing For example, when cerium(iv) ammonium nitrate, a much stronger oxidizing agent than a copper salt, was employed for the asymmetric α-oxyamination of an aldehyde, recycling peptide catalyst 1 drastically decreased yield and enantioselectivity. In case of 2a, the reaction gave the product with 71% yield and 89% ee in the first reuse of 1, but with 14% yield and 58% ee in the second reuse During the revision of this manuscript, Maruoka et al.
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