4-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).

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

PINESCHI, MAURO;CROTTI, PAOLO;
2004

Abstract

4-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).
Pineschi, Mauro; F., DEL MORO; Crotti, Paolo; F., Macchia
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/202172
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