A convenient preparation of 3,3,3-trifluoro-1-propynylamines and their Lewis acid catalyzed reaction with carbonyl compounds leading to (Z)-alpha-(trifluoromethyl)-alpha,beta-unsaturated amides

Authors
Mantani, T Shiomi, K Konno, T Ishihara, T Yamanaka, H
Citation
T. Mantani et al., A convenient preparation of 3,3,3-trifluoro-1-propynylamines and their Lewis acid catalyzed reaction with carbonyl compounds leading to (Z)-alpha-(trifluoromethyl)-alpha,beta-unsaturated amides, J ORG CHEM, 66(10), 2001, pp. 3442-3448
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
10
Year of publication
2001
Pages
3442 - 3448
Database
ISI
SICI code
0022-3263(20010518)66:10<3442:ACPO3A>2.0.ZU;2-9
Abstract
N,N-Dialkyl(3,3,3-trifluoro-1-propynyl)amines were readily prepared by a th ree-step procedure starting from commercially available 2,2,3,3,3 -pentaflu oropropanol. These fluorinated alkynylamines reacted smoothly with a variet y of aldehydes or ketones in the presence of a catalytic amount of Lewis ac id and;molecular sieves 4 Angstrom at ambient temperature to produce the co rresponding alpha-(trifluoromethyl)-alpha,beta -unsaturated amides in good to excellent yields with high Z-stereoselectivity.