Lithiation of cinnamyl chloride: Stereoselective synthesis of propargylic oxiranes and aziridines

Authors
Florio, S Troisi, L Capriati, V Suppa, G
Citation
S. Florio et al., Lithiation of cinnamyl chloride: Stereoselective synthesis of propargylic oxiranes and aziridines, EUR J ORG C, (22), 2000, pp. 3793-3797
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
22
Year of publication
2000
Pages
3793 - 3797
Database
ISI
SICI code
1434-193X(200011):22<3793:LOCCSS>2.0.ZU;2-1
Abstract
Propargylic oxiranes 4a-e and aziridines 8a-c have been prepared from cinna myl chloride through lithiation-alkylation with alpha -halo carbonyl compou nds and alpha -chloro imines, respectively. The reaction with substituted a lpha -halo carbonyl compounds and alpha -chloro imines proved to be highly E diastereoselective.