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Asymmetric induction in intramolecular ene reactions of 1,7-dienes

โœ Scribed by Lutz F Tietze; Uwe Beifuss


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
239 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Chiral, double-activated enophiles in 1,7-dienes 6a -d undergo thermal and Lewis-acid catalyzed intramolecular ene reactions yielding trans-cyclohexanes 7a-d and 8a-d.


๐Ÿ“œ SIMILAR VOLUMES


Intramolecular ene reactions, III. Diast
โœ Tietze, Lutz F. ;BeifuรŸ, Uwe ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 962 KB

The I .74iencs 3ac with a double-activated cnophile moiety undzrgo thermal and zinc bromide catalyzed intramolecular ene rcactions lcading to rrurts-1.2-disubstitutcd cyclohexanes 4a-c in up to 8 9 9 ~ yield, highly diastcrcoselectively. The synthesis of cyclulicxaim from 1.7-diencs has not been fca

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Ablracf: A chid a-cyanovinyl sulfoxide served as an efficient chiral enophile in a Lewis acid-catalyzed intramolecular ene reaction. Use of diethylaluminum chloride as a catalyst provided extremely high stereoselectivity in this ene reaction. Based on the stereochemical results obtained, a mechanist