The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters

Ming Chang P. Yeh; Paul Knochel

doi:10.1016/S0040-4039(01)80511-6

The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters

Ming Chang P. Yeh^*
, Paul Knochel

^*此作品的通信作者

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

119 引文斯高帕斯（Scopus）

摘要

The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me₃SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters. In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97% pure (E)-2-trimethylsilyl ethylenic esters.

原文	英語
頁（從 - 到）	4799-4802
頁數	4
期刊	Tetrahedron Letters
卷	30
發行號	36
DOIs	https://doi.org/10.1016/S0040-4039(01)80511-6
出版狀態	已發佈 - 1989
對外發佈	是

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

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10.1016/S0040-4039(01)80511-6

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abstract = "The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64\% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters. In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97\% pure (E)-2-trimethylsilyl ethylenic esters.",

author = "Yeh, \{Ming Chang P.\} and Paul Knochel",

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AU - Knochel, Paul

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Y1 - 1989

N2 - The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters. In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97% pure (E)-2-trimethylsilyl ethylenic esters.

AB - The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters. In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97% pure (E)-2-trimethylsilyl ethylenic esters.

UR - https://www.scopus.com/pages/publications/0000064055

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AN - SCOPUS:0000064055

SN - 0040-4039

VL - 30

SP - 4799

EP - 4802

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters

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