Magnesiated unsaturated silylated cyanohydrins as synthetic equivalents of aromatic and heterocyclic Grignard reagents bearing a ketone or an aldehyde

Ching Yuan Liu, Hongjun Ren, Paul Knochel

研究成果: 雜誌貢獻期刊論文同行評審

25 引文 斯高帕斯(Scopus)

摘要

The preparation of iodo-substituted aryl, heteroaryl, or cycloalkenyl ketones as silylated cyanohydrins allows the smooth performance of an l/Mg-exchange using i-PrMgCl·LiCl. A facile deprotection of the resulting functionalized products obtained by a reaction with electrophiles (acid chlorides, allylic bromide, benzylidene-p-toluenesulfonamide, and 3-iodocyclohexenone) produces polyfunctional ketones in good overall yields. This sequence can be extended to aromatic iodoaldehydes. In these cases, the deprotection of the silylated cyanohydrin functionality is best performed with aqueous CuSO4 under basic conditions.

原文???core.languages.en_GB???
頁(從 - 到)617-619
頁數3
期刊Organic Letters
8
發行號4
DOIs
出版狀態已出版 - 16 2月 2006

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