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Synfacts 2010(6): 0686-0686  
DOI: 10.1055/s-0029-1219967
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iron(II)-Catalyzed Selective Grignard Addition to Vinyl Oxiranes

Contributor(s): Hisashi Yamamoto, Patrick Brady
T. Hata, R. Bannai, M. Otsuki, H. Urabe*
Tokyo Institute of Technology, Yokohama, Japan
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Publikationsdatum:
20. Mai 2010 (online)

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Significance

The authors describe a useful entry to stereodefined homoallylic alcohols. With the ­exception of the ethynyl Grignard reagent, all other reagents give a single diastereomer. This method provides complimentary regioselectivity to copper-catalyzed addition, which furnishes allylic alcohols rather than homoallylic alcohols.