NEW APPLICATIONS OF N-ACYLIMINIUM PRECURSORS - TETRACARBONLIRON-MEDIATED STEREOSELECTIVE ALKYLATIONS OF 5-(R)-ISOPROPOXY-3-PYRROLIN-2-ONES

Authors
DEKONING H HIEMSTRA H MOOLENAAR MJ SPECKAMP WN
Citation
H. Dekoning et al., NEW APPLICATIONS OF N-ACYLIMINIUM PRECURSORS - TETRACARBONLIRON-MEDIATED STEREOSELECTIVE ALKYLATIONS OF 5-(R)-ISOPROPOXY-3-PYRROLIN-2-ONES, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (9), 1998, pp. 1729-1737
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
9
Year of publication
1998
Pages
1729 - 1737
Database
ISI
SICI code
1434-193X(1998):9<1729:NAONP->2.0.ZU;2-G
Abstract
Lewis acid catalyzed allylic substitutions with several nucleophiles a t C-5 of the cis-tetracarbonyliron complexes of N-acetyl- and N-tosyl- 5-(R) -isopropoxy-3-pyrrolin-2-ones occur highly regio- and stereosele ctively. The results are interpreted as being indicative of the interm ediacy of a ( pi-allyl)tetracarbonyliron cation, with possible precedi ng formation of an N-acyl- or an N-tosyliminium ion.