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Diastereofacial selectivity in the Diels-Alder reaction of 5(S)-E-5,6-O-isopropyliden-hex-3-en-2-one with cyclopentadiene

✍ Scribed by Guido Galley; Clemens Mügge; Peter G. Jones; Michael Pätzel

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 307 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00307-b

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✦ Synopsis

The effect of temperature, catalyst and pressure on the outcome of the Diels-Alder reaction of 5(S)-E-5,6-O-isopropyliden-hex-3-en-2-one with cyclopentadiene was investigated. All four possible Diels-Alder adducts were isolated and characterized on the basis of single crystal X-ray analysis and NMR experiments. Et:AICI was found to be the most effective catalyst to give exclusively the endo-isomers.

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