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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
Rhodium-Catalyzed Arylzincation of Terminal Allenes Providing Allylzinc Reagents and Its Application to Versatile Three-Component Coupling Reaction
J. Am. Chem. Soc.  2010,  132:  8878-8879  
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Publication History

Publication Date:
22 September 2010 (online)

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Key words

terminal allenes - three-component reaction - arylzincation - rhodium

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.

Comment

Multicomponents allow an easy one-pot access to molecular complexity. Multicomponent reactions involving allenes have recently attracted increased attention due to their efficiency. The high stereoselectivity of this reaction makes it a very valuable tool for modern synthesis.

Review: S. Ma Chem. Rev. 2005, 105, 2829-2871.

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