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

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)617-619
Number of pages3
JournalOrganic Letters
Volume8
Issue number4
DOIs
StatePublished - 16 Feb 2006

Fingerprint

Dive into the research topics of 'Magnesiated unsaturated silylated cyanohydrins as synthetic equivalents of aromatic and heterocyclic Grignard reagents bearing a ketone or an aldehyde'. Together they form a unique fingerprint.

Cite this