Bruno Linclau

Summary

Affiliation: University of Southampton
Country: UK

Publications

  1. pmc An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols
    Jérôme Graton
    CEISAM UMR CNRS 6230, Faculte des Sciences et des Techniques, Universite de Nantes, 2, rue de la Houssinière BP 92208, 44322 Nantes Cedex 3, France
    Angew Chem Int Ed Engl 51:6176-80. 2012
  2. doi request reprint Enantioselective synthesis of tetrafluorinated ribose and fructose
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton, UK
    Org Biomol Chem 7:803-14. 2009
  3. ncbi request reprint Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK
    Angew Chem Int Ed Engl 51:1232-5. 2012
  4. doi request reprint The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Carbohydr Res 346:1129-39. 2011
  5. ncbi request reprint Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6- dihydroxy-2,8-dioxabicyclo[3.3.0]octane
    Bruno Linclau
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, U K
    Org Lett 8:5821-4. 2006
  6. ncbi request reprint Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
    Alessandra Chighine
    School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, United Kingdom
    J Org Chem 74:4753-62. 2009
  7. ncbi request reprint A stereoselective cyclization to carbafuranose derivatives starting from 1,4-bis-epoxides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 7:5183-6. 2005
  8. doi request reprint A linchpin carbacyclization approach for the synthesis of carbanucleosides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 73:9197-206. 2008
  9. ncbi request reprint Ready synthetic access to enantiopure allylic α(F)-branched fluoroalkenes
    Florent Larnaud
    Laboratoire de Chimie Moleculaire et Thioorganique, UMR CNRS 6507 and FR3038, ENSICAEN, Universite de Caen Basse Normandie, 6 boulevard du Marechal Juin, 14050 Caen, France, and Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U K
    Org Lett 15:2450-3. 2013
  10. ncbi request reprint A practical synthesis of a high-loading solid-supported IBX amide for the oxidation of alcohols
    Patrick Lecarpentier
    Combinatorial Centre of Excellence, School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK
    Mol Divers 9:341-51. 2005

Collaborators

  • Serge Van Calenbergh
  • Tim Elliott
  • Dirk Elewaut
  • A James Boydell
  • Leo M H Leung
  • Stefano Crosignani
  • Clement Q Fontenelle
  • Florent Larnaud
  • Jérôme Graton
  • Mark Light
  • Vincent Foucher
  • Alessandra Chighine
  • Leo Leung
  • Roxana S Timofte
  • Vicky Gibson
  • Mark Bradley
  • Patrick Lecarpentier
  • Matthew Conroy
  • Xavier Pannecoucke
  • Thomas Poisson
  • Thierry Lequeux
  • Julien Malassis
  • Emmanuel Pfund
  • Zhong Wang
  • Anne Marie Brossard
  • Daniela Gonçalves Monteiro
  • Jean Yves Le Questel
  • Marinus B Groen
  • Benedetta Guizzardi
  • Marie Claire Arnal
  • Aymen Al-Shamkhani
  • Cyrille Tomassi
  • Tony Williams
  • Joern Werner
  • Tine Decruy
  • Christian Ottensmeier
  • Katrien Van Beneden
  • Mark E Light
  • Victoria Vinader
  • Delphine Launay
  • Martin J Jeffery
  • Eva Bürkstümmer

Detail Information

Publications18

  1. pmc An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols
    Jérôme Graton
    CEISAM UMR CNRS 6230, Faculte des Sciences et des Techniques, Universite de Nantes, 2, rue de la Houssinière BP 92208, 44322 Nantes Cedex 3, France
    Angew Chem Int Ed Engl 51:6176-80. 2012
  2. doi request reprint Enantioselective synthesis of tetrafluorinated ribose and fructose
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton, UK
    Org Biomol Chem 7:803-14. 2009
    ..A perfluoroalkylidene lithium mediated cyclisation approach for the enantioselective synthesis of a tetrafluorinated aldose (ribose) and of a tetrafluorinated ketose (fructose), both in the furanose and in the pyranose form, is described...
  3. ncbi request reprint Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK
    Angew Chem Int Ed Engl 51:1232-5. 2012
    ..In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center...
  4. doi request reprint The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Carbohydr Res 346:1129-39. 2011
    ..There is one close OH⋯F contact, which is likely to arise from the crystal packing. NMR studies show that the two anomers also adopt a (4)C(1) conformation in solution (D(2)O, CDCl(3))...
  5. ncbi request reprint Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6- dihydroxy-2,8-dioxabicyclo[3.3.0]octane
    Bruno Linclau
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, U K
    Org Lett 8:5821-4. 2006
    ..An efficient, enantioselective synthesis of a disubstituted bis-THF scaffold 5 is described, as well as an efficient differentiation of the 1,3-diol unit. [reaction: see text]..
  6. ncbi request reprint Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
    Alessandra Chighine
    School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, United Kingdom
    J Org Chem 74:4753-62. 2009
    ....
  7. ncbi request reprint A stereoselective cyclization to carbafuranose derivatives starting from 1,4-bis-epoxides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 7:5183-6. 2005
    ....
  8. doi request reprint A linchpin carbacyclization approach for the synthesis of carbanucleosides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 73:9197-206. 2008
    ..Both methods relied on Mitsunobu chemistry, and the first example of the Mukaiyama modification of the Mitsunobu reaction involving nucleobases as nucleophiles is reported...
  9. ncbi request reprint Ready synthetic access to enantiopure allylic α(F)-branched fluoroalkenes
    Florent Larnaud
    Laboratoire de Chimie Moleculaire et Thioorganique, UMR CNRS 6507 and FR3038, ENSICAEN, Universite de Caen Basse Normandie, 6 boulevard du Marechal Juin, 14050 Caen, France, and Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U K
    Org Lett 15:2450-3. 2013
    ..Convenient access to homochiral fluoroalkenes is described via a Julia-Kocienski olefination reaction. The required homochiral fluorosulfone is synthesized by a Mitsunobu reaction from readily available enantiopure secondary alcohols. ..
  10. ncbi request reprint A practical synthesis of a high-loading solid-supported IBX amide for the oxidation of alcohols
    Patrick Lecarpentier
    Combinatorial Centre of Excellence, School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK
    Mol Divers 9:341-51. 2005
    ..Oxidation of a range of alcohols to the corresponding carbonyl compounds proved very straightforward using 1.2 equiv of the resin. Recycling of the resin was also possible with minimal loss of activity after two reoxidations...
  11. ncbi request reprint Enantioselective synthesis of tetrafluoroethylene-containing monosaccharides
    A James Boydell
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Angew Chem Int Ed Engl 43:5677-9. 2004
  12. doi request reprint A novel, versatile D-->BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone
    Vincent Foucher
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 12:680-3. 2010
    ..The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization...
  13. doi request reprint Enantioselective synthesis of tetrafluorinated glucose and galactose
    Roxana S Timofte
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ
    Org Lett 10:3673-6. 2008
    ....
  14. ncbi request reprint Short synthesis of enantiopure C2-symmetric 1,2:4,5-diepoxypentane and "pseudo"-C2-symmetric 3-azido-1,2:4,5-diepoxypentane from arabitol
    A James Boydell
    Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 68:8252-5. 2003
    ..Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis...
  15. ncbi request reprint Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines
    Clement Q Fontenelle
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    J Org Chem 79:4186-95. 2014
    ..Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity. ..
  16. pmc Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Beilstein J Org Chem 6:62. 2010
    ..Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed...
  17. doi request reprint Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000
    Leo Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Org Lett 10:4433-6. 2008
    ..The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation...
  18. ncbi request reprint Microwaves, supported-reagents and parallel synthesis: isocyanide and ester synthesis
    Stefano Crosignani
    Combinatorial Centre of Excellence, Department of Chemistry, University of Southampton, Highfield, Southampton, UK
    Mol Divers 7:203-10. 2003
    ..Not only were reaction times dramatically reduced but the transformations were less prone to side reactions and decomposition...