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Chemoenzymatic Dynamic Kinetic Resolution of Allylic Alcohols: A Highly Enantioselective Route to Acyloin Acetates
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2007 (Engelska)Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 9, nr 17, s. 3401-3404Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to give the corresponding acylated acyloins in high yields without loss of chiral information.

Ort, förlag, år, upplaga, sidor
2007. Vol. 9, nr 17, s. 3401-3404
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-24335DOI: 10.1021/ol071395vISI: 000248658800052OAI: oai:DiVA.org:su-24335DiVA, id: diva2:197250
Tillgänglig från: 2007-05-30 Skapad: 2007-05-23 Senast uppdaterad: 2022-02-25Bibliografiskt 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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Bäckvall, Jan-E.

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