Highly diastereoselective Diels?Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone
✍ Scribed by Adams, Harry; Jones, Simon; Ojea-Jimenez, Isaac
- Book ID
- 119950209
- Publisher
- Royal Society of Chemistry
- Year
- 2006
- Tongue
- English
- Weight
- 289 KB
- Volume
- 4
- Category
- Article
- ISSN
- 1477-0520
- DOI
- 10.1039/B603819K
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📜 SIMILAR VOLUMES
Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr 2 Lewis acid conditions with reversal regiochemistry but similar ~-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9.
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
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