Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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
Supramolecular activation in triggered cascade inversion
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
2008 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, 1359-1361 p.Article in journal (Refereed) Published
Abstract [en]

An unexpected activation effect from combinations of anionic reagent and amine base resulted in dramatic rate enhancements in multiple carbohydrate cascade inversion.

Place, publisher, year, edition, pages
2008. 1359-1361 p.
Keyword [en]
SELF-REPLICATING SYSTEMS; DOMINO REACTIONS; ALTROSIDES; RECEPTORS; CHEMISTRY; EPOXIDES; NITRITE; ANIONS; ALPHA
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-9888DOI: 10.1039/b717301fISI: 000254352900029Scopus ID: 2-s2.0-41749125230OAI: oai:DiVA.org:kth-9888DiVA: diva2:139849
Note
QC 20100709Available from: 2009-01-27 Created: 2009-01-27 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Open this publication in new window or tab >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study, the effects of the neighboring group on the Lattrell-Dax inversion were explored. A new carbohydrate/anion host-guest system was discovered and the ambident reactivity of the nitrite anion was found to cause a complicated behavior of the reaction. It has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, restricting the nitrite N-attack, thus resulting in O-attack only and inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed by use of double parallel and double serial inversion. A supramolecularly activated, triggered cascade reaction was also developed. This cascade reaction is triggered by a deprotonation process that is activated by anions. It was found that the anions can activate this reaction following their hydrogen bonding tendencies to the hydroxyl group in aprotic solvents.

Place, publisher, year, edition, pages
Stockholm: KTH, 2009. 59 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Keyword
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Public defence
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100709Available from: 2009-01-27 Created: 2009-01-26 Last updated: 2012-02-23Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopushttp://www.rsc.org/publishing/journals/CC/article.asp?doi=b717301f

Search in DiVA

By author/editor
Dong, HaiPei, ZhichaoRamström, Olof
By organisation
Chemistry
In the same journal
Chemical Communications
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 59 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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