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Enantioselective Synthesis of the Excitatotry Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid.

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Title: Enantioselective Synthesis of the Excitatotry Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid.
Authors: Bradley, Daniel M., Mapitse, Renameditswe, Thomson, Nicholas M., Hayes, Christopher J.
Source: Journal of Organic Chemistry. 11/1/2002, Vol. 67 Issue 22, p7613. 5p. 5 Diagrams.
Subjects: Excitatory amino acids, Carbenes
Abstract: An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed. [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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DbLabel: Engineering Source
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PubType: Academic Journal
PubTypeId: academicJournal
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  Data: Enantioselective Synthesis of the Excitatotry Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid.
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  Data: <searchLink fieldCode="AR" term="%22Bradley%2C+Daniel+M%2E%22">Bradley, Daniel M.</searchLink><br /><searchLink fieldCode="AR" term="%22Mapitse%2C+Renameditswe%22">Mapitse, Renameditswe</searchLink><br /><searchLink fieldCode="AR" term="%22Thomson%2C+Nicholas+M%2E%22">Thomson, Nicholas M.</searchLink><br /><searchLink fieldCode="AR" term="%22Hayes%2C+Christopher+J%2E%22">Hayes, Christopher J.</searchLink>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 11/1/2002, Vol. 67 Issue 22, p7613. 5p. 5 Diagrams.
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  Data: <searchLink fieldCode="DE" term="%22Excitatory+amino+acids%22">Excitatory amino acids</searchLink><br /><searchLink fieldCode="DE" term="%22Carbenes%22">Carbenes</searchLink>
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  Label: Abstract
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  Data: An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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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/jo025892v
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      – Code: eng
        Text: English
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        PageCount: 5
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      – SubjectFull: Excitatory amino acids
        Type: general
      – SubjectFull: Carbenes
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      – TitleFull: Enantioselective Synthesis of the Excitatotry Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid.
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            NameFull: Bradley, Daniel M.
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            NameFull: Mapitse, Renameditswe
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            NameFull: Thomson, Nicholas M.
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              Text: 11/1/2002
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              Y: 2002
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