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Direct Organoctalytic Asymmetric α-Oxidation of Ketones with Iodosobenzene and N-sulfonyloxaziridine
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2004 Inngår i: Tetrahedron letters, ISSN 0040-4039, Vol. 46, nr 12, s. 2053-2057Artikkel i tidsskrift (Fagfellevurdert) Published
sted, utgiver, år, opplag, sider
2004. Vol. 46, nr 12, s. 2053-2057
Identifikatorer
URN: urn:nbn:se:su:diva-23699OAI: oai:DiVA.org:su-23699DiVA, id: diva2:194026
Merknad
Part of urn:nbn:se:su:diva-449Tilgjengelig fra: 2005-04-07 Laget: 2005-04-07bibliografisk kontrollert
Inngår i avhandling
1. Direct Amino Acid-Catalyzed Enantioselective α-Oxidation Reactions and Asymmetric de novo Synthesis of Carbohydrates
Åpne denne publikasjonen i ny fane eller vindu >>Direct Amino Acid-Catalyzed Enantioselective α-Oxidation Reactions and Asymmetric de novo Synthesis of Carbohydrates
2005 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The ability of amino acids to form nucleophilic enamines with aldehydes and ketones has been used in the development of asymmetric α-oxidation reactions with electrophilic oxidizing agents. Singlet molecular oxygen has for the first time been asymmetrically incorporated into aldehydes and ketones, and the products were isolated as their corresponding diols in good yields and ee’s. Organocatalytic α-oxidations of cyclic ketones with iodosobenzene and N-sulfonyloxaziridine were also possible and furnished after reduction the product diols in generally low yields and in low to good ee’s. Amino acids have also been shown to catalyze the formation of carbohydrates by sequential aldol reactions. For example, proline and hydroxy proline mediate a highly selective trimerisation of α-benzyloxyacetaldehyde into allose, which was obtained in >99 % ee. Non linear effect studies of this reaction revealed the largest permanent nonlinear effect observed in a proline-catalyzed reaction to date. Moreover, polyketides were also assembled in a similar fashion by an amino acid-catalyzed one-pot reaction, and was successful for the trimerisation of propionaldehyde, however the sequential cross aldol reactions suffered from lower selectivities. This problem was overcome by the development of a two-step synthesis that enabled the formation of a range of polyketides with excellent selectivities from a variety of aldehydes. The method furnishes the polyketides via the shortest route reported and in comparable product yields to most multi-step synthesis. All polyketides were isolated as single diastereomers with >99 % ee. Based on the observed amino acid-catalysis, amino acids are thought to have taken part in the prebiotic formation of tetroses and hexoses.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2005
Emneord
Organo catalysis
HSV kategori
Identifikatorer
urn:nbn:se:su:diva-449 (URN)91-7155-035-6 (ISBN)
Disputas
2005-04-28, sal G, Arrheniuslaboratorierna, Svante Arrhenius väg 14-18, Stockholm, 10:00
Opponent
Veileder
Tilgjengelig fra: 2005-04-07 Laget: 2005-04-07bibliografisk kontrollert

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Totalt: 46 treff
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