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Direct, Catalytic Synthesis of Carbapenams via Cycloaddition/Rearrangement Cascade Reaction: Unexpected Acetylenes' Structure Effect.

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Title: Direct, Catalytic Synthesis of Carbapenams via Cycloaddition/Rearrangement Cascade Reaction: Unexpected Acetylenes' Structure Effect.
Authors: Mames, Adam1, Stecko, Sebastian1, Mikołajczyk, Paulina1, Soluch, Magdalena1, Furman, Bartłomiej1, Chnlielewski, Marek1 chmiel@icho.edu.pl
Source: Journal of Organic Chemistry. 11/19/2010, Vol. 75 Issue 22, p7580-7588. 9p. 9 Diagrams, 5 Charts.
Subjects: Acetylene, Chemical reactions, Oxygen, Copper salts, Chemical bonds
Abstract: Reactions of acetylenes derived from glyceraldehyde and propargyl aldehyde show remarkable reactivity in Kinugasa cycloaddition/rearrangement cascade process catalyzed by Cu(I) ion. Reactions proceed by formation of a rigid dinuclear copper(I) complex in which each copper ion is coordinated to one or both oxygen atoms in the acetylene molecule and to both triple bonds. It has been demonstrated that one oxygen atom can be replaced by the phenyl ring, which is able to coordinate the copper ion by the aromatic sextet. Kinugasa reactions that proceed in a high yield can also be performed in the presence of a catalytic amount of the copper salt to provide products in an acceptable yield without a decrease of diastereoselectivity. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Direct, Catalytic Synthesis of Carbapenams via Cycloaddition/Rearrangement Cascade Reaction: Unexpected Acetylenes' Structure Effect.
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 11/19/2010, Vol. 75 Issue 22, p7580-7588. 9p. 9 Diagrams, 5 Charts.
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  Data: <searchLink fieldCode="DE" term="%22Acetylene%22">Acetylene</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Oxygen%22">Oxygen</searchLink><br /><searchLink fieldCode="DE" term="%22Copper+salts%22">Copper salts</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+bonds%22">Chemical bonds</searchLink>
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  Data: Reactions of acetylenes derived from glyceraldehyde and propargyl aldehyde show remarkable reactivity in Kinugasa cycloaddition/rearrangement cascade process catalyzed by Cu(I) ion. Reactions proceed by formation of a rigid dinuclear copper(I) complex in which each copper ion is coordinated to one or both oxygen atoms in the acetylene molecule and to both triple bonds. It has been demonstrated that one oxygen atom can be replaced by the phenyl ring, which is able to coordinate the copper ion by the aromatic sextet. Kinugasa reactions that proceed in a high yield can also be performed in the presence of a catalytic amount of the copper salt to provide products in an acceptable yield without a decrease of diastereoselectivity. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/jo101355h
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      – Code: eng
        Text: English
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        PageCount: 9
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      – SubjectFull: Acetylene
        Type: general
      – SubjectFull: Chemical reactions
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      – SubjectFull: Oxygen
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              Text: 11/19/2010
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