en
Scientific article
English

Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds

Published inTetrahedron letters, vol. 34, no. 44, p. 7049-7052
Publication date1993
Abstract

The amine catalyzed coupling reaction of acrylic derivatives with benzaldehydes (Baylis-Hillman reaction) is more efficient when the arene is complexed to the electrophilic Cr(CO)3 group. Reactions with planar chiral o-substituted benzaldehyde complexes are highly diastereoselective. 3-Hydroxy-2-methylenealkanoic acid derivatives can be obtained efficiently and with very high enantiomeric excess from readily accessible enantiomerically pure complexes. The configuration of the benzylic stereogenic center relative to the planar chirality of the arene complex was determined in one case by an X-ray structural analysis. The reaction has been extended to an o-anisaldehydeimine complex.

Citation (ISO format)
KUNDIG, Ernst Peter et al. Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds. In: Tetrahedron letters, 1993, vol. 34, n° 44, p. 7049–7052. doi: 10.1016/S0040-4039(00)61594-0
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0040-4039
614views
0downloads

Technical informations

Creation05/17/2010 2:56:00 PM
First validation05/17/2010 2:56:00 PM
Update time03/14/2023 3:29:04 PM
Status update03/14/2023 3:29:04 PM
Last indexation01/15/2024 7:58:37 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack