Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 29, Pages 4988-4998Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800702
Keywords
Bicycles; Domino reactions; Fragmentation; Metathesis
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Funding
- French Research Ministry
- Universite Paul Cezanne
- CNRS [UMR 6263]
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A series of cis-alpha,gamma-difunctionalized five-membered cyclic beta-oxo esters have been chemo-, regio- and diastereoselectively prepared through an efficient domino anionic ring-cleavage/ring-reconstitution/alkylation sequence including a 1,3-shift of the ester group. These unsaturated substrates were successfully engaged in various ring-closing metatheses to provide a reliable access to functionalized bicyclo[4.2.1]nonanes, precursors of cyclooctanoids following the selective fragmentation of the one-carbon bridge. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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