Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Show others and affiliations
2012 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 1, no 3, 134-139 p.Article in journal (Refereed) Published
Abstract [en]

A highly enantioselective, metal-free cascade reaction between di-1,2-N-protected hydrazine and α,β-unsaturated aldehydes is disclosed. The catalytic, asymmetric cascade transformation is a direct entry to 3-hydroxypyrazolidine and 3-allylpyrazolidine derivatives in one step and two steps, respectively, with >19:1 d.r. and 98–99 % ee using simple chiral pyrrolidines as catalysts.

Place, publisher, year, edition, pages
2012. Vol. 1, no 3, 134-139 p.
Keyword [en]
1, 4-selectivity, asymmetric catalysis, cascade reactions, hemiaminals, metal-free catalysis, pyrazolidines
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-94675DOI: 10.1002/open.201200015OAI: oai:DiVA.org:su-94675DiVA: diva2:654792
Available from: 2013-10-08 Created: 2013-10-08 Last updated: 2017-12-06Bibliographically approved
In thesis
1. Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
Open this publication in new window or tab >>Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In biological systems, most of the active organic molecules are chiral. Some of the main constituents of living organisms are amino acids and sugars. They exist predominantly in only one enantiomerically pure form. For example, our proteins are built-up by L-amino acids and as a consequence they are enatiomerically pure and will interact in different ways with enantiomers of chiral molecules. Indeed, different enantiomers or diastereomers of a molecule could often have a drastically different biological activity. It is of paramount importance in organic synthesis to develop new routes to control and direct the stereochemical outcome of reactions. The aim of this thesis is to investigate new protocols for the synthesis of complex chiral molecules using simple, environmentally friendly proline-based organocatalysts. We have investigated, the aziridination of linear and branched enals, the stereoselective synthesis of β-amino acids with a carbene co-catalyst, the synthesis of pyrazolidines, the combination of heterogeneous transition metal catalysis and amine catalysis to deliver cyclopentenes bearing an all-carbon quaternary stereocenter and a new heterogeneous dual catalyst system for the carbocyclization of enals. The reactions presented in this thesis afforded the corresponding products with high levels of chemo-, diastero- and enantioselectivity.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2013. 75 p.
Keyword
Organocatalysis, Asymmetric Catalysis, Heterogeneous Catalysis, Aziridines, Pyrazolidines, Cyclopentanes
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-94680 (URN)978-91-7447-781-8 (ISBN)
Public defence
2013-12-04, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 5: Submitted. 

Available from: 2013-11-12 Created: 2013-10-08 Last updated: 2014-09-24Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Deiana, LucaSun, JunliangCórdova, Armando
By organisation
Department of Organic ChemistryStructural Chemistry
In the same journal
ChemistryOpen
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 62 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf