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limonoids from Khaya senegalensis

Sami A. Khalid1, Gerda M. Friedrichsen, Arsalan Kharazmi

  • 1Department of Pharmacognosy, Faculty of Pharmacy, University of Khartoum, P.O. Box 1996, Khartoum, Sudan

Phytochemistry
|November 17, 2001
PubMed

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...