Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry

This paper reports efficient procedures for the preparation of optically active dibromide, diazide, diamine, and unsaturated diesters derived from a chiral bicyclic diol with C-2 symmetry namely (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol 3. 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 (N,N'-dicyclohexylurea) from reactions carried out following the DCC/DMAP method are described. (C) 2010 Elsevier Ltd. All rights reserved.