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Synfacts 2006(2): 0156-0156
DOI: 10.1055/s-2005-924788
DOI: 10.1055/s-2005-924788
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Cu-Catalyzed Stereoselective Reaction of Allylic Carbonates with Diboronate
H. Ito, C. Kawakami, M. Sawamura*
Hokkaido University, Japan
Further Information
Publication History
Publication Date:
23 January 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200602/lookinside/thumbnails/10.1055-s-2005-924788-1.jpg)
Significance
Allylboron derivatives are important synthetic intermediates, for instance, for the stereoselective allylation of carbonyl compounds. This is a new and very attractive method for a diastereoselective preparation of allylboron pinacolates, starting from readily available chiral allylic carbonates. The reaction conditions are extremely mild, and this process offers an excellent tolerance of functional groups. In the presence of Xanthphos as a ligand, the reaction is completely γ-selective. As expected, (Z)- and (E)-allylic carbonates with the same configuration of the chiral center give the opposite enantiomers of the product.