Preparation and application of iron-substituted (Z)-enals: Synthesis of 5-substituted alpha,beta-butenolides

Authors
Mikulas, M Moller, C Rust, S Wierschem, F Amrhein, P Ruck-Braun, K
Citation
M. Mikulas et al., Preparation and application of iron-substituted (Z)-enals: Synthesis of 5-substituted alpha,beta-butenolides, J PRAK CHEM, 342(8), 2000, pp. 791-803
Citations number
34
Categorie Soggetti
Chemistry
Journal title
JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY
ISSN journal
14369966 → ACNP
Volume
342
Issue
8
Year of publication
2000
Pages
791 - 803
Database
ISI
SICI code
1436-9966(2000)342:8<791:PAAOI(>2.0.ZU;2-Q
Abstract
A reaction sequence furnishing cyclic beta-[eta (C5H5)-C-5(CO)(2)Fe]-substi tuted enals 5 starting from beta -keto esters 1 is described. Organolithium s were found to react smoothly with the iron-substituted enals yielding alp ha,beta -butenolides 6 by an intramolecular cyclocarbonylation of the lithi umalkoxide initially formed. The influence of e.g. the reaction temperature and the solvent on the reaction cascade is discussed. A reaction mechanism is proposed.