PaaSicats: Powerful catalysts for asymmetric epoxidation of enones. Novel syntheses of alpha-arylpropanoic acids including (S)-fenoprofen

Authors
Carde, L Davies, H Geller, TP Roberts, SM
Citation
L. Carde et al., PaaSicats: Powerful catalysts for asymmetric epoxidation of enones. Novel syntheses of alpha-arylpropanoic acids including (S)-fenoprofen, TETRAHEDR L, 40(29), 1999, pp. 5421-5424
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5421 - 5424
Database
ISI
SICI code
0040-4039(19990716)40:29<5421:PPCFAE>2.0.ZU;2-J
Abstract
Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of Two enones is reported. Treatment o f these epoxides with trimethylaluminium in moist dichloromethane generates the alpha-hydroxy-beta-methylketones, with inversion of configuration. Dia stereoselective reduction of the ketone moiety followed by oxidative cleava ge generates alpha-arylpropanoic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.