uu.seUppsala University Publications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • 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
The use of nonactivated iminodienophiles in the stereoselective aza-Diels-Alder reaction
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
2004 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 15, no 3, 445-452 p.Article in journal (Refereed) Published
Abstract [en]

This paper describes the preparation of nitrogen-containing bicycles by the aza-Diels–Alderreaction ofnonactivatediminodienophiles and cyclopentadiene. Readily available starting materials such as (S)-(−)-lactate and l-amino acids were used for the preparation of chiral aldehydes with high enantiomeric excess. The improved oxidation procedure by Dess–Martin periodinane was employed for the synthesis of l-alanine derived phthalimide protected aldehyde 14, which was difficult to obtain in high enantiomeric excess by other methods. The influence of different Lewis acids on the stereoselectivity of the aza-Diels–Alderreactionwas also investigated: It was found that the use of a combination of BF3·Et2O and TFA in the cycloaddition leads to complete racemization of the imine prepared from 14 whereas the use of TiCl4 gives the cycloaddition products 17a and 17b with high enantioselectivity (90%).

Place, publisher, year, edition, pages
Elsevier , 2004. Vol. 15, no 3, 445-452 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-7338DOI: 10.1016/j.tetasy.2003.12.011OAI: oai:DiVA.org:uu-7338DiVA: diva2:131115
Available from: 2007-11-12 Created: 2007-11-12 Last updated: 2017-12-14Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text
By organisation
Organic Chemistry
In the same journal
Tetrahedron: asymmetry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 509 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • 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