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Synfacts 2006(6): 0603-0603  
DOI: 10.1055/s-2006-941772
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Carbometallation of Propargylic Alcohols by Grignard Reagents

Contributor(s): Paul Knochel, Andrei Gavryushin
Z. Lu, S. Ma*
Zhejiang University, Hangzhou and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

Herein, an optimized protocol for the highly regioselective carbometallation of terminal secondary propargylic alcohols by alkylmagnesium bromides is described. The reaction is catalyzed by copper salts and is completely anti-stereoselective. The conservation of the chiral information is observed, if an enantiopure substrate is used. The resulting vinylmagnesium species can be used further in Kumada coupling reaction or trapped by iodine to form (Z)-alkenyl iodides. For the latter, some further synthetic transformations are desribed.