TY - JOUR
T1 - Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate, an easy starting point for the enantioselective preparation of trans-cyclohexene-4,5-dicarboxylate derivatives by Diels-Alder reaction
AU - Palomino-Schätzlein, Martina
AU - Virgili, Albert
AU - Jaime, Carlos
AU - Molins, Elies
PY - 2006/12/11
Y1 - 2006/12/11
N2 - Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate has been synthesized from fumaric acid and enantiopure Pirkle alcohol. The Diels-Alder reaction with different dienes employing different reaction conditions was assayed, with high diastereomeric excesses obtained. The structure and geometry of the cycloadducts was analyzed by NMR, molecular mechanics and X-ray diffraction. Hydrolysis made it possible to obtain the enantioenriched trans-cyclohexene-4,5-dicarboxylate derivatives and allow us to recover chiral auxiliary. © 2007 Elsevier Ltd. All rights reserved.
AB - Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate has been synthesized from fumaric acid and enantiopure Pirkle alcohol. The Diels-Alder reaction with different dienes employing different reaction conditions was assayed, with high diastereomeric excesses obtained. The structure and geometry of the cycloadducts was analyzed by NMR, molecular mechanics and X-ray diffraction. Hydrolysis made it possible to obtain the enantioenriched trans-cyclohexene-4,5-dicarboxylate derivatives and allow us to recover chiral auxiliary. © 2007 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tetasy.2006.11.047
DO - 10.1016/j.tetasy.2006.11.047
M3 - Article
VL - 17
SP - 3237
EP - 3243
IS - 23
ER -