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

Martina Palomino-Schätzlein, Albert Virgili, Carlos Jaime, Elies Molins

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4 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)3237-3243
JournalTetrahedron Asymmetry
Volume17
Issue number23
DOIs
Publication statusPublished - 11 Dec 2006

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