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Supramolecular activation in triggered cascade inversion
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
2008 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, s. 1359-1361Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
2008. s. 1359-1361
Nyckelord [en]
SELF-REPLICATING SYSTEMS; DOMINO REACTIONS; ALTROSIDES; RECEPTORS; CHEMISTRY; EPOXIDES; NITRITE; ANIONS; ALPHA
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-9888DOI: 10.1039/b717301fISI: 000254352900029Scopus ID: 2-s2.0-41749125230OAI: oai:DiVA.org:kth-9888DiVA, id: diva2:139849
Anmärkning
QC 20100709Tillgänglig från: 2009-01-27 Skapad: 2009-01-27 Senast uppdaterad: 2017-12-14Bibliografiskt granskad
Ingår i avhandling
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Öppna denna publikation i ny flik eller fönster >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2009. s. 59
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Nyckelord
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Disputation
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning
QC 20100709Tillgänglig från: 2009-01-27 Skapad: 2009-01-26 Senast uppdaterad: 2012-02-23Bibliografiskt granskad

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Förlagets fulltextScopushttp://www.rsc.org/publishing/journals/CC/article.asp?doi=b717301f

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