ONE-POT SYNTHESIS OF 4-AMINOBICYCLO[2.2.2]OCTAN-2-ONES

Authors
WEIS R SCHWEIGER K SEEBACHER W BELAJ F
Citation
R. Weis et al., ONE-POT SYNTHESIS OF 4-AMINOBICYCLO[2.2.2]OCTAN-2-ONES, Tetrahedron, 54(46), 1998, pp. 14015-14022
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
46
Year of publication
1998
Pages
14015 - 14022
Database
ISI
SICI code
0040-4020(1998)54:46<14015:OSO4>2.0.ZU;2-M
Abstract
Dialkylammonium rhodanides and benzylidene acetone give racemic (6RS,7 RS)-4-dialkylaminobicyclo[2.2.2]octan-2-ones in a one-pot reaction in good yields. The mechanism of the reaction includes a Diels-Alder step , The structures are established by NMR spectra and a single crystal s tructure analysis. The compounds consist of cations of racemates of op tically active (6R,7R)- and ialkylamino-6,7-diphenylbicyclo[2.2.2]octa n-2-ones and isothiocyanate anions. (C) 1998 Elsevier Science Ltd. All rights reserved.