The synthesis of substituted amino[2.2]paracyclophanes.
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.
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
Krishanthi P
KP
Jayasundera
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz and Vrije Universiteit Amsterdam, The Netherlands.
Disraëli N M
DN
Kusmus
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz and Ecole Nationale Supérieure de Chimie de Rennes, France.
Lise
L
Deuilhé
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
Leonie
L
Etheridge
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
Zane
Z
Farrow
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
David J
DJ
Lun
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
Gurpreet
G
Kaur
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand. g.j.rowlands@massey.ac.nz.
Gareth J
http://orcid.org/0000-0002-8661-5860
GJ
Rowlands