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Synfacts 2006(2): 0134-0134  
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

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Schwier, V. Gevergyan*
University of Chicago, USA
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Publication History

Publication Date:
23 January 2006 (online)

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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.