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(S)-Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2006 Inngår i: Chemistry: a European Journal, ISSN 0947-6539, Vol. 12, nr 1, s. 225-232Artikkel i tidsskrift (Fagfellevurdert) Published
sted, utgiver, år, opplag, sider
2006. Vol. 12, nr 1, s. 225-232
Identifikatorer
URN: urn:nbn:se:su:diva-25585OAI: oai:DiVA.org:su-25585DiVA, id: diva2:200012
Merknad
Part of urn:nbn:se:su:diva-8298Tilgjengelig fra: 2008-11-20 Laget: 2008-11-04bibliografisk kontrollert
Inngår i avhandling
1. Enantioselective Synthesis of Sec-Alcohol Derivatives and Diols via Combined Ruthenium and Enzyme Catalysis
Åpne denne publikasjonen i ny fane eller vindu >>Enantioselective Synthesis of Sec-Alcohol Derivatives and Diols via Combined Ruthenium and Enzyme Catalysis
2008 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The first part of this thesis describes the synthesis of enantiopure secondary alcohol derivatives. These syntheses are carried out via the combination of an enzyme as a resolution catalyst and a ruthenium catalyst as a racemization catalyst, in what is called dynamic kinetic resolution (DKR). By varying the resolution catalyst enantio-complementary processes can be obtained. A lipase (PS-C II) catalyzed DKR of γ-hydroxyamides gave the corresponding (R)-acetates in high yields and with high enantioselectivity. The synthetic usefulness of these obtained (R)-acetates was demonstrated by the synthesis of (R)-5-methyltetrahydrofurane-2-one. A protease (Subtilisin Carlsberg) catalyzed DKR of various secondary alcohols gave the corresponding (S)-acetates in high yields and with high enantioselectivity. In the second part of this thesis the DKR process has been extended into a dynamic kinetic asymmetric transformation (DYKAT) of diols. Various 1,5- and 1,4-diols were transformed into enantiopure diacetates in a lipase (CALB and PS-C II) catalyzed DYKAT. The synthetic utility of the obtained enantiopure diacetates were demonstrated by the synthesis of various enantiopure disubstituted heterocycles.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2008
Emneord
catalysis, kinetic resolution, ruthenium catalyst, Dynamic kinetic resolution, Dynamic Kinetic Asymmetric Transformation
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-8298 (URN)978-91-7155-778-0 (ISBN)
Disputas
2008-12-12, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Opponent
Veileder
Tilgjengelig fra: 2008-11-20 Laget: 2008-11-04 Sist oppdatert: 2012-06-26bibliografisk kontrollert

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