Chiral organolithium species: determination of the rate of cyclization andextent of racemization

Authors
Coldham, I Vennall, GP
Citation
I. Coldham et Gp. Vennall, Chiral organolithium species: determination of the rate of cyclization andextent of racemization, CHEM COMMUN, (17), 2000, pp. 1569-1570
Citations number
40
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
17
Year of publication
2000
Pages
1569 - 1570
Database
ISI
SICI code
1359-7345(2000):17<1569:COSDOT>2.0.ZU;2-T
Abstract
The rate of intramolecular carbolithiation onto an unactivated alkene to gi ve a six-membered ring has been determined and follows first order kinetics with a half life of similar to 90 min at 23 degrees C; this allows signifi cant racemization using a chiral organolithium species, although good level s of optical purity are obtained with a phenylthio-substituted alkene.