View in EDS

Asymmetric Kinugasa Reaction of Cyclic Nitrones and Nonracemic Acetylenes.

Saved in:
Bibliographic Details
Title: Asymmetric Kinugasa Reaction of Cyclic Nitrones and Nonracemic Acetylenes.
Authors: Stecko, Sebastian1, Mames, Adam1, Furman, Bartlomiej1, Chmielewski, Marek1 chmiel@icho.edu.pl
Source: Journal of Organic Chemistry. 4/17/2009, Vol. 74 Issue 8, p3094-3100. 7p.
Subjects: Chemical research, Chemical reactions, Proton transfer reactions, Organic synthesis, Acetylene, Enantiomers
Abstract: Kinugasa reactions between chiral acetylenes and five-membered nitrones, achiral and bearing a stereogenic center in both enantiomeric forms, proceed in moderate to good yield with high diastereoselectivity affording mostly one dominant product. The first step of the reaction is controlled by the configuration of the nitrone, whereas the protonation of intermediate enolate in the second step depends mainly on the configuration of the bridgehead carbon atom formed in the first step. In the case of the mismatched pair, the configuration at the C-6 center of the carbapenam skeleton may also be affected by the configuration of the stereogenic center in the acetylene portion. [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.)
Database: Engineering Source
FullText Text:
  Availability: 0
Header DbId: egs
DbLabel: Engineering Source
An: 39241280
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Asymmetric Kinugasa Reaction of Cyclic Nitrones and Nonracemic Acetylenes.
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Stecko%2C+Sebastian%22">Stecko, Sebastian</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Mames%2C+Adam%22">Mames, Adam</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Furman%2C+Bartlomiej%22">Furman, Bartlomiej</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Chmielewski%2C+Marek%22">Chmielewski, Marek</searchLink><relatesTo>1</relatesTo><i> chmiel@icho.edu.pl</i>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 4/17/2009, Vol. 74 Issue 8, p3094-3100. 7p.
– Name: Subject
  Label: Subjects
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Chemical+research%22">Chemical research</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Proton+transfer+reactions%22">Proton transfer reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Acetylene%22">Acetylene</searchLink><br /><searchLink fieldCode="DE" term="%22Enantiomers%22">Enantiomers</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Kinugasa reactions between chiral acetylenes and five-membered nitrones, achiral and bearing a stereogenic center in both enantiomeric forms, proceed in moderate to good yield with high diastereoselectivity affording mostly one dominant product. The first step of the reaction is controlled by the configuration of the nitrone, whereas the protonation of intermediate enolate in the second step depends mainly on the configuration of the bridgehead carbon atom formed in the first step. In the case of the mismatched pair, the configuration at the C-6 center of the carbapenam skeleton may also be affected by the configuration of the stereogenic center in the acetylene portion. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  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.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=39241280
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1021/jo900121x
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 7
        StartPage: 3094
    Subjects:
      – SubjectFull: Chemical research
        Type: general
      – SubjectFull: Chemical reactions
        Type: general
      – SubjectFull: Proton transfer reactions
        Type: general
      – SubjectFull: Organic synthesis
        Type: general
      – SubjectFull: Acetylene
        Type: general
      – SubjectFull: Enantiomers
        Type: general
    Titles:
      – TitleFull: Asymmetric Kinugasa Reaction of Cyclic Nitrones and Nonracemic Acetylenes.
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Stecko, Sebastian
      – PersonEntity:
          Name:
            NameFull: Mames, Adam
      – PersonEntity:
          Name:
            NameFull: Furman, Bartlomiej
      – PersonEntity:
          Name:
            NameFull: Chmielewski, Marek
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 17
              M: 04
              Text: 4/17/2009
              Type: published
              Y: 2009
          Identifiers:
            – Type: issn-print
              Value: 00223263
          Numbering:
            – Type: volume
              Value: 74
            – Type: issue
              Value: 8
          Titles:
            – TitleFull: Journal of Organic Chemistry
              Type: main
ResultId 1