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Synfacts 2006(5): 0474-0474  
DOI: 10.1055/s-2006-934345
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Co(II)-Catalyzed Cross-Coupling of Alkyl Iodides and Arylmagnesium Reagents

Contributor(s): Mark Lautens, Andrew Martins
H. Ohmiya, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

In the presence of a Co(II)-diamine catalyst system, a variety of secondary alkyl halides were diastereoselectively coupled with arylmagnesium reagents to form C-C bonds. Diastereoselectivity ranged from poor to excellent and was optimal with R1 = (+)-isomenthyl as a chiral auxiliary. In addition to these results, the non-dia­stereoselective coupling of a variety of alkyl halides was demonstrated, as well as the total synthesis of a synthetic prostaglandin.