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

doi:10.1021/om00017a041

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

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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 language	English
Pages (from-to)	1788-1794
Number of pages	7
Journal	Organometallics
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/om00017a041
Publication status	Published - 1994 May 1

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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

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.",

author = "Yeh, {Ming Chang P.} and Hwu, {Chong Chen} and Ueng, {Chuen Her} and Lue, {Huei Lin}",

year = "1994",

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T1 - Michael Addition Reactions of the Highly Functionalized Zinc-Copper Reagents RCu(CN)ZnI to (Tropone)iron Tricarbonyl Promoted by Boron Trifluoride Etherate

AU - Yeh, Ming Chang P.

AU - Hwu, Chong Chen

AU - Ueng, Chuen Her

AU - Lue, Huei Lin

PY - 1994/5/1

Y1 - 1994/5/1

N2 - 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.

AB - 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.

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

Abstract

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