(2:2) Paracyclophane (2.2.PCs) are systems in which the benzene rings are held closely, face to face so that independent rotation of either ring is impossible. Consequently all mono- and many poly-substituted 2.2.PCs are linearly chiral. Because the systems are chemically and chirally very stable they are ideal as substrates on which to design chiral reagents, auxiliaries and catalysts and for incorporation into otherwise non-chiral moieties.
One result of our studies is the production of unique homochiral 2.2PC aminoacids. The project will build on this as follows:
(i) Improved synthesis of all possible 2.2PC amino-acids will be sought. (ii) The amino-acids will be incorporated into linear and cyclic peptides, so affecting their topology and lipophilicity.
(iii) The corresponding amino-alcohols lactams and related compounds will be investigated as chiral catalysts for metal catalysed reactions (eg Michael Reactions) and as chiral auxiliaries for a wide variety of reactions such as carbanion reactions, Diels-Alder and Michael reactions.