Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

Ming Chang P. Yeh, Chong Chen Hwu, Chuen Her Ueng, Huei Lin Lue

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Abstract

The zinc-copper reagents RCu(CN)ZnI, containing various functional groups such as a cyanide, ester, thio ester or benzyl, react with (tropone)iron tricarbonyl in the presence of an excess of boron trifluoride etherate to afford the Michael adducts in excellent yields. Cyano-substituted 1.4-adducts undergo an intramolecular cyclization reaction in situ, leading to highly functionalized bicyclo[5.3.0]decane and-[5.4.0]undecane derivatives, whereas treatments of an ester-substituted 1.4-adduct with lithium diisopropylamide (LDA) under an atmosphere of carbon monoxide furnishs a highly functionalized bridged bicyclo[4.2.1] nonenecarboxylic acid derivative in 88 % yield.

Original languageEnglish
Pages (from-to)1788-1794
Number of pages7
JournalOrganometallics
Volume13
Issue number5
DOIs
Publication statusPublished - 1994 May 1

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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