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Synthesis of Optically Active Derivatives of Bicyclic Chiral Diols with C2 Symmetry
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1  Departamento de Química and INQUISUR (UNS-CONICET), Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina

Abstract: Efficient synthesis, besides other, of dibromide, diazide, diamine and diesters derived from (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (3), a chiral bicyclic diol with C2 symmetry, was developed. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU from reactions carried out following DCC/DMAP mehod are described.
Keywords: C2 symmetry, 9,10-dihydro-9,10-ethanoanthracene, chiral ligands