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
✦ LIBER ✦
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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