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  • 1.
    Díaz-Álvarez, Alba E.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Mesas Sanchez, Laura
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Dinér, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Non-Enzymatic Dynamic Kinetic Resolution of Secondary Aryl Alcohols: Planar Chiral Ferrocene and Ruthenium Catalysts in Cooperation2013Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, nr 2, s. 502-504Artikel i tidskrift (Refereegranskat)
  • 2.
    Díaz-Álvarez, Alba E.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Mesas-Sánchez, Laura
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Dinér, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC. KTH-Royal Institute of Technology.
    Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst2014Ingår i: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, nr 9, s. 14273-14291Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

  • 3.
    Mesas Sánchez, Laura
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Organocatalytic Acylation for the Kinetic Resolution of Secondary Aryl Alcohols: Synthetic Applications and Mechanistic Studies2014Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
    Abstract [en]

    The research described in this thesis focuses on the catalytic acylative kinetic resolution (KR) of aromatic secondary alcohols, using a planar-chiral 4-(dimethylamino)pyridine (DMAP) organocatalyst.

    In the first part of this thesis, the substrate scope of the above mentioned process was expanded to aromatic secondary alcohols that contain an extra functional group in the alkyl moiety, such as 1,2-azido alcohols, 2-hydroxy-2-aryl-ethylphosphonates and 2-hydroxy-2-aryl esters. Thus, the preparation of highly functionalized compounds in their enantiomerically pure form with excellent enantiomeric excess (up to 99% ee) was achieved. Furthermore, the synthetic applicability of this methodology was illustrated through the synthesis of two high value compounds, (R)-Pronethalol and (S)-3-hydroxy-N-methyl-3-phenylpropanamide, which is an immediate precursor of bioactive molecules such as (S)-Fluoxetine.

    The second part of this thesis deals with the mechanistic study of the acylative KR catalyzed by the planar-chiral DMAP derivative. Reaction Progress Kinetic Analysis methodology was used in the investigation of the reaction mechanism, probing that no notable product inhibition or decomposition of the catalyst occurs in the studied system. The reaction rate showed fractional order dependence on the concentration of both reactants. Furthermore, NMR spectroscopy was utilized to study the equilibrium between the different catalyst states, which explains the measured kinetics of the reaction.

    Delarbeten
    1. Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst
    Öppna denna publikation i ny flik eller fönster >>Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst
    2013 (Engelska)Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, nr 2, s. 753-757Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee).

    Nyckelord
    Non-enzymatic kinetic resolution, 1, 2-Azidoalcohols, Planar-chiral DMAP derivative catalyst, Ferrocenyl catalyst
    Nationell ämneskategori
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-189450 (URN)10.1016/j.tet.2012.10.077 (DOI)000314371800045 ()
    Tillgänglig från: 2013-01-02 Skapad: 2013-01-02 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
    2. Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst
    Öppna denna publikation i ny flik eller fönster >>Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst
    2014 (Engelska)Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, nr 24, s. 3807-3811Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

    Nyckelord
    Non-enzymatic kinetic resolution, 2-Hydroxy-2-arylethylphosphonates, Planar chiral DMAP derivative catalyst
    Nationell ämneskategori
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-227994 (URN)10.1016/j.tet.2014.03.102 (DOI)000336710200010 ()
    Tillgänglig från: 2014-07-04 Skapad: 2014-07-02 Senast uppdaterad: 2017-12-05Bibliografiskt granskad
    3. Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst
    Öppna denna publikation i ny flik eller fönster >>Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst
    2014 (Engelska)Ingår i: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, nr 9, s. 14273-14291Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

    Nyckelord
    non-enzymatic kinetic resolution, β-hydroxy esters, planar-chiral DMAP catalyst, ferrocenyl catalyst
    Nationell ämneskategori
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-224444 (URN)10.3390/molecules190914273 (DOI)000343093100085 ()25215586 (PubMedID)
    Anmärkning

    Alba E. DiazIvarez and Laura Mesas-Sanchez contributed equally to this work.

    Tillgänglig från: 2014-10-08 Skapad: 2014-05-12 Senast uppdaterad: 2017-12-05Bibliografiskt granskad
    4. A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst
    Öppna denna publikation i ny flik eller fönster >>A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst
    2015 (Engelska)Ingår i: CHEMISTRY-A EUROPEAN JOURNAL, ISSN 0947-6539, Vol. 21, nr 14, s. 5623-5631Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    A detailed kinetic analysis for the acetylation of 1-phenylethanol with acetic anhydride catalyzed by the planar chiral DMAP catalyst (–)-1 is presented. The study include a computational investigation of the potential energy surface including the rate-limiting and stereoselective transitionstates at the DFT level of theory. The kinetic study suggests that the reaction proceeds with first order in catalyst and in 1-phenylethanol, while the acetic anhydride shows a fractional order. The fractional order is racionalized based on an equilibrium between the free and the acetylated catalyst.

    Nyckelord
    Reaction progress kinetic analysis, DFT calculation
    Nationell ämneskategori
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-233714 (URN)10.1002/chem.201405793 (DOI)000352504500041 ()25677932 (PubMedID)
    Tillgänglig från: 2014-10-09 Skapad: 2014-10-08 Senast uppdaterad: 2015-05-12Bibliografiskt granskad
  • 4.
    Mesas-Sanchez, Laura
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Diaz-Alvarez, Alba E.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Koukal, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Diner, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst2014Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, nr 24, s. 3807-3811Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

  • 5.
    Mesas-Sánchez, Laura
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Dinér, Peter
    KTH Royal Institute of Technology.
    A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst2015Ingår i: CHEMISTRY-A EUROPEAN JOURNAL, ISSN 0947-6539, Vol. 21, nr 14, s. 5623-5631Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A detailed kinetic analysis for the acetylation of 1-phenylethanol with acetic anhydride catalyzed by the planar chiral DMAP catalyst (–)-1 is presented. The study include a computational investigation of the potential energy surface including the rate-limiting and stereoselective transitionstates at the DFT level of theory. The kinetic study suggests that the reaction proceeds with first order in catalyst and in 1-phenylethanol, while the acetic anhydride shows a fractional order. The fractional order is racionalized based on an equilibrium between the free and the acetylated catalyst.

  • 6.
    Mesas-Sánchez, Laura
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Díaz-Álvarez, Alba Estrella
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Dinér, Peter
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst2013Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, nr 2, s. 753-757Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee).

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