Highly Alkyl-Selective Addition to Ketones with Magnesium Ate Complexes Derived from Grignard Reagents

Manabu Hatano, Tokihiko Matsumura and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan, Email: ishiharacc.nagoya-u.ac.jp

M. Hatano, T. Matsumura, K. Ishihara, Org. Lett., 2005, 7, 573-576.

DOI: 10.1021/ol047685i

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Abstract

The nucleophilicity of magnesium ate complexes derived from Grignard reagents and alkyllithiums is remarkably increased compared to that of the original RLi or RMgX, while the basicity of R₃MgLi is decreased, which allows a highly efficient alkyl-selective addition to ketones.

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Key Words

Grignard Reaction, 1,2-Additions

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ID: J54-Y2005-170