Enantioselective nucleophilic opening of meso epoxides by organolithium reagents (pg 1165, 1998)

Authors
Alexakis, A Vrancken, E Mangeney, P
Citation
A. Alexakis et al., Enantioselective nucleophilic opening of meso epoxides by organolithium reagents (pg 1165, 1998), SYNLETT, (12), 1998, pp. 1461
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
1998
Database
ISI
SICI code
0936-5214(199812):12<1461:ENOOME>2.0.ZU;2-H
Abstract
Aryl lithium reagents, complexed with (-)-sparteine, react enantioselective ly with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiom eric excess, though moderate (27-87%), is the best in the literature for su ch a reaction. Activation by BF3.OEt2 is needed, and is compatible with a d iamine such as (-)-sparteine.