Fumarate of (S,S)-α,α′-bis(trifluoromethyl)-1,8- anthracenedimethanol. A chiral macrocycle for the Diels-Alder reaction with cyclopentadiene

The synthesis and structural study of the fumarate of (S,S)-α, α′-bis(trifluoromethyl)-1,8-anthracenedimethanol by NMR spectroscopy are reported. The conformational study of the 13-membered macrocycle is presented. The cited alcohol is assayed as a chiral auxiliary in a Diels-Alder reaction with cyclopentadiene, and after methanolysis, provides the norbornene derivative with high enanfioselectivity. © 2006 American Chemical Society.