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The synthesis of substituted amino[2.2]paracyclophanes

Abstract : Two methodologies for the formation of substituted amino[2.2]paracyclophane derivatives were developed. The first involves the direct amination of bromo[2.2]paracyclophanes with sodium azide. This permits the synthesis of simple mono- and disubstituted derivatives but fails to give sterically congested pseudo-gem derivatives. A ‘one-pot’ oxidation-Lossen rearrangement of [2.2]paracyclophane oximes provides access to a range of amino[2.2]paracyclophanes including the most efficient synthesis of the pseudo-gem planar chiral amino acid yet reported.
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Krishanthi P. Jayasundera, Disraëli N. M. Kusmus, Lise Deuilhé, Leonie Etheridge, Zane Farrow, et al.. The synthesis of substituted amino[2.2]paracyclophanes. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2016, 14 (46), pp.10848-10860. ⟨10.1039/C6OB02150F⟩. ⟨hal-01558325⟩

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