Highly alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents

Manabu Hatano; Tokihiko Matsumura; Kazuaki Ishihara

doi:10.1021/ol047685i

Highly alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents

Org Lett. 2005 Feb 17;7(4):573-6. doi: 10.1021/ol047685i.

Authors

Manabu Hatano¹, Tokihiko Matsumura, Kazuaki Ishihara

Affiliation

¹ Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.

PMID: 15704897
DOI: 10.1021/ol047685i

Abstract

A highly efficient alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents and alkyllithiums is described. The nucleophilicity of R in R3MgLi is remarkably increased compared to that of the original RLi or RMgX, while the basicity of R3MgLi is decreased. Furthermore, a highly R-selective addition to ketones is demonstrated using RMe2MgLi in place of R3MgLi. [reaction: see text]