Regio- and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles

Gary D. Fallon, Neil J. Fitzmaurice, W. Roy Jackson, Patrick Perlmutter

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19 Citations (Scopus)

Abstract

By varying the steric bulk of silicon substituents attached to alk-1-ynes it is possible to control, to a high degree, the regiochemical outcome of nickel(0)-catalysed hydrocyanations of alk-1-ynes: the crystal structure of one adduct is included which establishes that the stereochemical outcome of the reaction is a result of addition of HCN to the alkyne to give an (E)-product; overall, these results constitute a simple method for the preparation of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles.

Original languageEnglish
Pages (from-to)4-5
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number1
DOIs
Publication statusPublished - 1 Jan 1985

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