Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl.LiCl |
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Authors: | Ren Hongjun Krasovskiy Arkady Knochel Paul |
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Institution: | Department Chemie, Ludwig-Maximilians-Universit?t, Butenandtstrasse 5-13, 81377 München, Germany. |
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Abstract: | Acyclic functionalized alkenyl iodides are converted with high stereoselectivity to the corresponding functionalized alkenylmagnesium derivatives by the reaction with i-PrMgCl.LiCl between -40 and -20 degrees C. Functional groups such as a nitrile, chloride, iodide, and ester are readily tolerated. The conversion of an alkenyl iodide bearing a keto group to the corresponding silylated cyanohydrin allows preparation of the corresponding Grignard reagent affording, after acylation and deprotection, unsaturated 1,4-diketones. |
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