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Large Scale Metalloenzymatic Dynamic Kinetic Resolution of (rac)-1-Phenylethanol
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Manuskript (Annet vitenskapelig)
Identifikatorer
URN: urn:nbn:se:su:diva-24337OAI: oai:DiVA.org:su-24337DiVA, id: diva2:197252
Merknad
Part of urn:nbn:se:su:diva-6876Tilgjengelig fra: 2007-05-30 Laget: 2007-05-23 Sist oppdatert: 2010-01-13bibliografisk kontrollert
Inngår i avhandling
1. Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
Åpne denne publikasjonen i ny fane eller vindu >>Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
2007 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis deals with the preparation of a new half-sandwich type ruthenium(II)- catalyst for racemization of optically active secondary alcohols and the development of a highly efficient method in combination with lipases such as Candida antarctica lipase B and Pseudomonas cepacia lipase for dynamic kinetic resolution of various functionalized alcohols under mild reaction conditions.

It was shown that the RuCl(CO)25-C5Ph5) complex can racemize optically active aliphatic and aromatic secondary alcohols at room temperature in rather short times. Different parameters, such as the nature of the catalyst, catalyst loading and solvent effect were studied. After the optimization steps, the Ru-catalyzed racemization of (S)-1-phenylethanol in the presence of Candida antarctica lipase B was also investigated. The compatibility of the metal- and enzyme-catalyzed reactions led to a highly efficient coupled catalytic system for transformation of racemic alcohols to their enantiomerically pure acetates. This protocol was applied for a wide range of secondary alcohols. It was shown that in the case of allylic alcohols the obtained enantiopure allylic acetates are useful compounds for synthesis of α-methyl carboxylic acids such as (R)-Flurbiprofen and acyloin acetates. Highly selective dynamic kinetic asymmetric transformation of 3,5-piperidine diol to deliver various 3,5-dioxygenated piperidines is also described.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2007. s. 66
Emneord
ruthenium, racemization, lipase, dynamic kinetic resolution, secondary alcohol, Candida antarctica lipase B
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-6876 (URN)978-91-7155-463-5 (ISBN)
Disputas
2007-06-20, Magnélisalen, Arrheniuslaboratoriet, Svante Arrhenius väg 12, Stockholm, 10:00
Opponent
Veileder
Tilgjengelig fra: 2007-05-30 Laget: 2007-05-23 Sist oppdatert: 2017-10-16bibliografisk kontrollert

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