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Synfacts 2009(9): 1002-1002
DOI: 10.1055/s-0029-1217670
DOI: 10.1055/s-0029-1217670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Generation and Applications of α-Chiral Allylic Stannanes
E. S. Schmidtmann, M. Oestreich*
Westfälische Wilhelms-Universitat Münster, Germany
Further Information
Publication History
Publication Date:
21 August 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200909/lookinside/thumbnails/10.1055-s-0029-1217670-1.jpg)
Significance
Previously, the authors have reported the copper-catalyzed reaction of soft bis(triorganosilyl) zinc reagents for carbon-silicon bond formation. In the present paper the authors apply this methodology to the use of bis(triorganostannyl) zinc reagents in the enantiospecific synthesis of all-carbon-substituted allylic stannanes. These stannanes could subsequently undergo either thermal or Lewis acid promoted SE2′ reactions with aldehydes to give anti- or syn-homoallylic alcohols in high diastereoselectivities with nearly complete chirality transfer.