Combining ring-closing metathesis and hydroformylation strategies: A novelapproach to spirocyclic gamma-butyrolactones

Authors
Schmidt, B Costisella, B Roggenbuck, R Westhus, M Wildemann, H Eilbracht, P
Citation
B. Schmidt et al., Combining ring-closing metathesis and hydroformylation strategies: A novelapproach to spirocyclic gamma-butyrolactones, J ORG CHEM, 66(23), 2001, pp. 7658-7665
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
23
Year of publication
2001
Pages
7658 - 7665
Database
ISI
SICI code
0022-3263(20011116)66:23<7658:CRMAHS>2.0.ZU;2-Y
Abstract
Di- or tetrahydropyrans with a vinyl side chain are obtained by diastereose lective ring-closing metathesis or by addition of vinylmagnesium chloride t o an appropriately functionalized tetrahy-dropyranone. The resulting allyli c alcohols are converted to spirocyclic hemiacetals under hydroformylation conditions. Oxidation yields the corresponding lactones.