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Highly diastereoselective Diels-Alder reaction of optically active ethyl 2-p-tolylsulfinylmethylenepropionate with cyclopentadiene

✍ Scribed by Toru Koizumi; Ichiro Hakamada; Eiichi Yoshii


Book ID
104242345
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
254 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis


Stereochemistry of the Diels-Alder reaction of ethyl Z-and E-2-ptolylsulfinylmethylenepropionate with cyclopentadiene has been studied. The high diastereoselectivity was observed especially in the case of exo-cycloaddition.

We have previously reported that (+)-(R)S p-tolyl vinyl sulfoxide 1 is a


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Highly diastereoselective diels-alder re
✍ I. Alonso; J.C. Carretero; J.L. Garcia Ruano 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 224 KB

The Diels-Alder reaction of (S)-Z-ptolylsulphinyl-2-cyclopentenone (and 2cyclohexcnone) with cyclopentadiene, catalized by AlCl3 and AlEtClz, occurs at room temperature with complete facial diastereoselectivity, but with moderate endo-exe selectivity. Substituted enantiomerically pure o,Bunsaturate