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Synfacts 2006(2): 0134-0134
DOI: 10.1055/s-2005-924816
DOI: 10.1055/s-2005-924816
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Trans- and cis-Selective Lewis Acid-Catalyzed Hydrogermylation of Alkynes
T. Schwier, V. Gevergyan*
University of Chicago, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200602/lookinside/thumbnails/10.1055-s-2005-924816-1.jpg)
Significance
The stereoselective formation of alkenes is an important organic transformation. This represents the first Lewis acid-catalyzed stereoselective hydrogermylation to date. Hydrogermylation of simple alkynes resulted in trans-alkene products, while the hydrogermylation of propiolates gave cis-alkene products. Adducts of this reaction (both trans and cis) were produced in extremely good yield (majority >99%) and complete selectivity. The transformation of the vinyl metal species to the corresponding vinyl halide (I or Br) was found to occur in high yields with retention of geometry.