The synthesis of substituted amino[2.2]paracyclophanes.
- Publisher:
- ROYAL SOC CHEMISTRY
- Publication Type:
- Journal Article
- Citation:
- Org Biomol Chem, 2016, 14, (46), pp. 10848-10860
- Issue Date:
- 2016-11-22
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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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