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High-yielding metalloenzymatic dynamic kinetic resolution of fluorinated aryl alcohols
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2007 (Engelska)Ingår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, nr 31, s. 5471-5474Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Dynamic kinetic resolution (DKR) of various fluorinated aryl alcohols by a combination of lipase-catalyzed enzymatic resolution with in situ ruthenium-catalyzed alcohol racemization is described. (R)-Selective Candida antarctica lipase B (CALB) was employed for transesterification of different fluoroaryl alcohols in DKR reactions delivering the corresponding acetates in high yield (97%) with excellent enantiomeric excess (98%).

Ort, förlag, år, upplaga, sidor
2007. Vol. 48, nr 31, s. 5471-5474
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-24336DOI: 10.1016/j.tetlet.2007.05.175ISI: 000248527400026OAI: oai:DiVA.org:su-24336DiVA, id: diva2:197251
Tillgänglig från: 2007-05-30 Skapad: 2007-05-23 Senast uppdaterad: 2017-12-13Bibliografiskt granskad
Ingår i avhandling
1. Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
Öppna denna publikation i ny flik eller fönster >>Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
2007 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: Institutionen för organisk kemi, 2007. s. 66
Nyckelord
ruthenium, racemization, lipase, dynamic kinetic resolution, secondary alcohol, Candida antarctica lipase B
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-6876 (URN)978-91-7155-463-5 (ISBN)
Disputation
2007-06-20, Magnélisalen, Arrheniuslaboratoriet, Svante Arrhenius väg 12, Stockholm, 10:00
Opponent
Handledare
Tillgänglig från: 2007-05-30 Skapad: 2007-05-23 Senast uppdaterad: 2017-10-16Bibliografiskt granskad

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