RUTHENIUM-CATALYZED REDOX TRANSFORMATION OF CINNAMALDEHYDE TO 3-PHENYLPROPIONIC ACID AND METHYL-ESTER

Authors
DEVRIES JG ROELFES G GREEN R
Citation
Jg. Devries et al., RUTHENIUM-CATALYZED REDOX TRANSFORMATION OF CINNAMALDEHYDE TO 3-PHENYLPROPIONIC ACID AND METHYL-ESTER, Tetrahedron letters, 39(45), 1998, pp. 8329-8332
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
45
Year of publication
1998
Pages
8329 - 8332
Database
ISI
SICI code
0040-4039(1998)39:45<8329:RRTOCT>2.0.ZU;2-P
Abstract
3-Phenylpropionic acid (2) is an intermediate for the anti-aids drug I ndinavir. The one step conversion of cinnamaldehyde (4) into 2 was att empted using homogeneous ruthenium catalysts. Use of [H2Ru(Ph3P)(4)] i nduced mainly decarbonylation of 4 to give styrene. Use of RuCl3/PCy3 gave a mixture of 2 and cinnamic acid (3). Performing the same reactio n in methanol, instead of water/dimethoxyethane mixtures afforded meth yl 3-phenylpropionate in 70% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.