The Alkylation of Ketone Enolates in the Presence of Triethanolamineborate. Control of Polyalkylation
- 1 January 1978
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 8 (1) , 9-14
- https://doi.org/10.1080/00397917808062176
Abstract
The formation of polyalkylated products is a major source of difficulty in the alkylation of ketone enolates. To some extent, this difficulty can be minimized by the use of lithium rather than sodium or potassium enolates.3 We have observed that triethylboron serves as an effective additive to minimize polyalkylation.4 For example, treatment of a THF solution of the sodium enolate of cyclohexanone with one equivalent of methyl iodide produces major amounts of dimethylated ketones, while the same reaction conducted in the presenceKeywords
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