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Synfacts 2010(10): 1171-1171  
DOI: 10.1055/s-0030-1258078
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Rhodium-Catalyzed Arylzincation of Terminal Allenes

Contributor(s): Paul Knochel, Tobias Thaler
Y. Yoshida, K. Murakami, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
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Publikationsdatum:
22. September 2010 (online)

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Significance

A novel efficient rhodium-catalyzed multicomponent reaction using an arylzinc iodide, a monosubstituted allene and an electrophile (E+) is reported. With acetonitrile and imines or aldehydes as electrophiles the use of Barbier-type conditions furnished the best yields. The reaction is highly diastereoselective, and thus allowed the synthesis of a stereodefined skipped polyene.