Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes

Authors
Zhou, HY Campbell, EJ Nguyen, ST
Citation
Hy. Zhou et al., Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes, ORG LETT, 3(14), 2001, pp. 2229-2231
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
14
Year of publication
2001
Pages
2229 - 2231
Database
ISI
SICI code
1523-7060(20010712)3:14<2229:ISACFT>2.0.ZU;2-N
Abstract
[GRAPHICS] Imidazolinium salts and their N heterocyclic carbene (NHC) derivatives cata lyze the alkylation of a variety of meso epoxides in the presence of trieth ylaluminum (yield = 70-90%), under mild conditions, Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization s ide reactions under extended reaction time. Preformed NHC.AlEt3 complexes a nd Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.