Synthesis of some new enantiopure [2.2]paracyclophanes bearing polycyclic aromatic subunits

The synthesis of some new optically active[2.2]paracyclophanes containing condensed polycyclic aromatic subunits is described. The Diels-Alder reactions of (S)-(+)-4-ethenyl[2.2]paracyclophane with 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone have been studied. The effect of the hydroxy group(s) on the reactivity of the dienophiles and on the regioselectivity of the Diels-Alder reaction has been discussed. A structural analysis of the reaction products by H-1 and C-13 NMR spectroscopy is also presented. (C) 2002 Elsevier Science Ltd. All rights reserved.