RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2006(12): 1252-1252
DOI: 10.1055/s-2006-955642
DOI: 10.1055/s-2006-955642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Rh(I)-Catalyzed Asymmetric Allylic Substitution with Boronic Acids
F. Ménard, T. M. Chapman, C. Dockendorff, M. Lautens*
University of Toronto, Canada
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955642-1.jpg)
Significance
The authors report a C-C coupling reaction between a simple meso-cyclic dicarbonate and a boronic acid to generate optically active cyclopentenol derivatives. The Rh(I) catalyst system allowed the asymmetric allylic substitution (AAS) with hard boronic acid nucleophiles that are air- and moisture-tolerant. The use of aryl nucleophiles complements the previous asymmetric Cu(II) variant to introduce alkyl groups (F. López, A. W. van Zijl, A. J. Minnaard, B. L. Feringa Chem. Commun. 2006, 409-411). The reaction showed reliably high enantioselectivity, regardless of the substitution of the aromatic ring.