4-amino(2.2)paracyclophane derivatives of chiral auxiliaries (I) ; Syntheses of unique chiral amino acids based on [2.2]paracyclophane (II)

• Main Author: Kidwell, H. V. W.
• Published: Swansea University 1999
• Subjects: 547.6
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.637795

The first project involved the synthesis of a series of N-acyl-N-alkyl-4-amino[2.2]paracyclophane derivatives and the formation of their enolates. This was followed by the reaction of the enolates with a series of different electrophiles at low temperature in order to determine the diastereoisomeric selectivity which could be achieved by the use of a [2.2]paracyclophane unit as a chiral auxiliary. The project also examined the development of more complex chiral auxiliaries which utilised additional functional groups to enhance the diasterofacial shielding capability of the [2.2]paracyclophane unit. The second project involved the development of a synthesis for 4-amino-13-carboxy[2.2]paracyclophane. This would be a homochiral amino acid containing a chiral[2.2]paracyclophane unit which relied for its chiral properties not from a discrete chiral centre but from the planar chirality of the [2.2]paracyclophane.