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

doi:10.1016/j.tetasy.2006.11.047

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

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 language	English
Pages (from-to)	3237-3243
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	23
DOIs	https://doi.org/10.1016/j.tetasy.2006.11.047
Publication status	Published - 11 Dec 2006

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@article{887ecc6ad10b421d856eb1bf7ee26514,

title = "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",

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. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

author = "Martina Palomino-Sch{\"a}tzlein and Albert Virgili and Carlos Jaime and Elies Molins",

year = "2006",

month = dec,

day = "11",

doi = "10.1016/j.tetasy.2006.11.047",

language = "English",

volume = "17",

pages = "3237--3243",

number = "23",

}

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. / Palomino-Schätzlein, Martina; Virgili, Albert ; Jaime, Carlos; Molins, Elies.

In: Tetrahedron Asymmetry, Vol. 17, No. 23, 11.12.2006, p. 3237-3243.

Research output: Contribution to journal › Article › Research › peer-review

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 -