The synthesis of substituted amino[2.2]paracyclophanes

Krishanthi P. Jayasundera (1) , Disraëli N. M. Kusmus (2, 1) , Lise Deuilhé (3, 1) , Leonie Etheridge (1) , Zane Farrow (1) , David J. Lun (1) , Gurpreet Kaur (1) , Gareth J. Rowlands (1)

1 Massey University
2 VU - Vrije Universiteit Amsterdam [Amsterdam]
3 ISCR - Institut des Sciences Chimiques de Rennes

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.

Domaines: Chimie

Krishanthi P. Jayasundera, Disraëli N. M. Kusmus, Lise Deuilhé, Leonie Etheridge, Zane Farrow, et al.. The synthesis of substituted amino[2.2]paracyclophanes. Organic & Biomolecular Chemistry, 2016, 14 (46), pp.10848-10860. ⟨10.1039/C6OB02150F⟩. ⟨hal-01558325⟩