Diastereoselective Friedel-Crafts reaction of alpha-trifluoromethyl iminesderived from chiral amines

Authors
Citation
Yf. Gong et K. Kato, Diastereoselective Friedel-Crafts reaction of alpha-trifluoromethyl iminesderived from chiral amines, TETRAHEDR-A, 12(15), 2001, pp. 2121-2127
Citations number
31
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
0957-4166 → ACNP
Volume
12
Issue
15
Year of publication
2001
Pages
2121 - 2127
Database
ISI
SICI code
0957-4166(20010829)12:15<2121:DFROAI>2.0.ZU;2-T
Abstract
The Friedel-Crafts reactions of chiral N-(2,2,2-trifluoroethylidene)-1-aryl ethylamines 1a and 1b with various electron-rich aromatic compounds were ex amined. The reactions proceeded readily at room temperature in the presence of BF3.Et2O. Substituted products 2-12 were obtained in low to very high s tereo selectivities (up to 100% d.e.). The absolute configuration of compou nd 12 was determined by X-ray analysis. Moreover, the chiral auxiliary from compounds 3 and 12 was selectively removed by palladium-catalyzed hydrogen olysis. (C) 2001 Elsevier Science Ltd. All rights reserved.