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Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines.

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Title: Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines.
Authors: Aher, Ravindra D.1, Kumar, B. Senthil1, Sudalai, Arumugam1 a.sudalai@ncl.res.in
Source: Journal of Organic Chemistry. 2/6/2015, Vol. 80 Issue 3, p2024-2031. 8p.
Subjects: Annulation, Pyrrolidine derivatives, Mannich reaction, Pyrrolidine synthesis, Asymmetric synthesis
Abstract: A highly efficient one-pot [4 + 1]-annulation process for the asymmetric synthesis of densely functionalized pyrrolidine derivatives is described. The in situ generated syn-Mannich adduct obtained via proline catalysis acts as a four-atom component, and Corey's sulfur ylide or ethyl bromoacetate acts as a one-atom carbon source to construct pyrrolidine units in a highly enantio- and diastereoselective manner. [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
An: 101084247
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines.
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  Data: <searchLink fieldCode="AR" term="%22Aher%2C+Ravindra+D%2E%22">Aher, Ravindra D.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Kumar%2C+B%2E+Senthil%22">Kumar, B. Senthil</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Sudalai%2C+Arumugam%22">Sudalai, Arumugam</searchLink><relatesTo>1</relatesTo><i> a.sudalai@ncl.res.in</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 2/6/2015, Vol. 80 Issue 3, p2024-2031. 8p.
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  Data: <searchLink fieldCode="DE" term="%22Annulation%22">Annulation</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrrolidine+derivatives%22">Pyrrolidine derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Mannich+reaction%22">Mannich reaction</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrrolidine+synthesis%22">Pyrrolidine synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Asymmetric+synthesis%22">Asymmetric synthesis</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: A highly efficient one-pot [4 + 1]-annulation process for the asymmetric synthesis of densely functionalized pyrrolidine derivatives is described. The in situ generated syn-Mannich adduct obtained via proline catalysis acts as a four-atom component, and Corey's sulfur ylide or ethyl bromoacetate acts as a one-atom carbon source to construct pyrrolidine units in a highly enantio- and diastereoselective manner. [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.)
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        Value: 10.1021/jo5028886
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      – Code: eng
        Text: English
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        PageCount: 8
        StartPage: 2024
    Subjects:
      – SubjectFull: Annulation
        Type: general
      – SubjectFull: Pyrrolidine derivatives
        Type: general
      – SubjectFull: Mannich reaction
        Type: general
      – SubjectFull: Pyrrolidine synthesis
        Type: general
      – SubjectFull: Asymmetric synthesis
        Type: general
    Titles:
      – TitleFull: Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines.
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            NameFull: Aher, Ravindra D.
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            NameFull: Kumar, B. Senthil
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            – D: 06
              M: 02
              Text: 2/6/2015
              Type: published
              Y: 2015
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            – TitleFull: Journal of Organic Chemistry
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