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English4-Alkyl-2,5,7-cyclooctatrienols with high enantiomeric purities (93-96% ee), obtained by an improved copper-phosphoramidite-catalyzed addition of dialkylzinc reagents to cyclooctatetraene monoepoxide, have been subjected to simple and practical manipulations. Simple esterification reactions are able to deliver new functionalized isomeric 8-alkyl-7-acyloxybicyclo[4.2.0]octa-2,4-dienes through a domino sequence of rearrangement reactions, in good yields. Moreover, new 4-alkyl-substituted-2,6-cyclooctadienones with high optical purity can be efficiently obtained from gramscale reactions by simple thermal treatment. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
| Autori interni: | |
| Autori: | M. PINESCHI; F. DEL MORO; CROTTI P; F. MACCHIA |
| Titolo: | Simple Synthetic Transformations of Highly Enantio-Enriched 4-Alkyl-2,5,7-cyclootatrienols into Functionalized Bicyclo[4.2.0]octa-2,4-dienes and 2,6-Cyclooctadienones |
| Anno del prodotto: | 2004 |
| Digital Object Identifier (DOI): | 10.1002/ejoc.200400355 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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http://hdl.handle.net/11568/202172
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