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Highly Efficient Ru-catalyzed Transfer Hydrogenation/Hydrogenation Procedure for 1,3-Cycloalkandiols using Controlled Microwave Heating
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Ansvarlig organisasjon
Manuskript (Annet vitenskapelig)
Identifikatorer
URN: urn:nbn:se:su:diva-25249OAI: oai:DiVA.org:su-25249DiVA, id: diva2:199233
Merknad
Part of urn:nbn:se:su:diva-789Tilgjengelig fra: 2006-01-04 Laget: 2006-01-04 Sist oppdatert: 2010-01-13bibliografisk kontrollert
Inngår i avhandling
1. Deracemization of Functionalized Alcohols via Combined Ruthenium and Enzyme Catalysis
Åpne denne publikasjonen i ny fane eller vindu >>Deracemization of Functionalized Alcohols via Combined Ruthenium and Enzyme Catalysis
2006 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The major part of this thesis describes the synthesis of enantiopure alcohols and diols by combining ruthenium-catalyzed racemization or epimerization and lipase-catalyzed asymmetric transformations. A minor part of this thesis is focused on ruthenium-catalyzed redox reactions for transfer hydrogenation of 1,3-cycloalkanediketones.

Kinetic resolution of racemic γ-hydroxy acid derivatives was performed via Pseudomonas cepacia lipase (PS-C)-catalyzed transesterification. γ-Hydroxy esters and γ-hydroxy amides were studied showing in higher selec-tivity and yields for the γ-hydroxy amides. The enzyme PS-C tolerates both variation in the chain length and different functionalities giving good to high enantioselectivity. Combining enzymatic kinetic resolution with a ruthenium-catalyzed racemization led to a dynamic kinetic resolution (DKR). The use of 2,4-dimethyl-3-pentanol as a hydrogen source to suppress ketone formation in the dynamic kinetic resolution increased the yields of the acetate product. The synthetic utility of this procedure was illustrated by the practical synthesis of the γ-lactone (R)-5-methyltetrahydrofuran-2-one.

A distereoselective transformation of cis/trans-1,3-cyclohexandiol using Candida antarctica lipase B (CALB)-catalyzed transesterification was of interest. Desymmetrization of cis-1,3-cyclohexanediol to the (R-monoacetate was successfully accomplished. Enantiopure (R,R)-diacetate was obtained from the (R)-monoacetate in a DYKAT process at room tem-perature. Metal- and enzyme-catalyzed transformation of cis/trans-1,3-cyclohexanediol using PS-C, gives a high diastereoselectivity for cis-diacetate. The (S)-mono-acetate was obtained from cis-diacetate by CALB-catalyzed hydrolysis. In addition, it was shown, by the use of deuterium-labeling that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

Ruthenium-catalyzed transfer hydrogenation of 1,3-cyclohexanedione under microwave heating was developed as an efficient and fast method for the preparation of 1,3-cycloalkandiols.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2006. s. 51
HSV kategori
Identifikatorer
urn:nbn:se:su:diva-789 (URN)91-7155-200-6 (ISBN)
Disputas
2006-01-26, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 13:00
Opponent
Veileder
Tilgjengelig fra: 2006-01-04 Laget: 2006-01-04 Sist oppdatert: 2012-06-26bibliografisk kontrollert

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