141
Views
9
CrossRef citations to date
0
Altmetric
ORIGINAL ARTICLE

Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters

, , &
Pages 272-278 | Received 09 May 2010, Accepted 11 Jun 2010, Published online: 01 Jul 2010

References

  • Anthonsen HW, Hoff BH, Anthonsen T. 1996. Calculation of enantiomer ratio and equilibrium constants in biocatalytic ping-pong bi-bi resolutions. Tetrahedron: Asymmetry 7:2633–2638.
  • Anthonsen T, Hoff BH. 1998. Resolution of derivatives of 1,2-propanediol with lipase B from Candida antarctica. Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio. Chem Phys Lipids 93:199–207.
  • Azumai T, Kurimoto I, Toda S, Minamii M. 1989. Preparation of optically active phenol derivatives as intermediates for liquid crystals. Japanese patent JP 03047143.
  • Azumai T, Minamii M. 1988. Optically active 4-benzyloxyaryl ethers as intermediates for liquid crystals. Japanese patent JP 01221341.
  • de Gonzalo, G, Lavandera, I, Brieva, R, Gotor, V. 2004. Enzymatic acylation reactions onω-hydroxy cyanohydrins. Tetrahedron 60:10525–10532.
  • de Maria PD, Carboni-Oerlemans C, Tuin B, Bargeman G, van der Meer A, van Gemert R. 2005. Biotechnological applications of Candida antarctica lipase A: state-of-the-art. J Mol Catal B Enzymatic 37:36–46.
  • Ericsson DJ, Kasrayan A, Johansson P, Bergfors T, Sandström AG, Bx00E4;ckvall J-E, Mowbray SL. 2008. X-ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation. J Mol Biol 376: 109–119.
  • Fuglseth E, Anthonsen T, Hoff B. 2006. New chiral building blocks from acetovanillone using lipases A and B from Candida antarctica. Tetrahedron: Asymmetry 17:1290–1295.
  • Fuglseth E, Sundby E, Bruheim P, Hoff BH. 2008a. Asymmetric reduction using (R)-MeCBS and determination of absolute configuration of para-substituted 2-fluoroarylethanols. Tetrahedron: Asymmetry 19:1941–1946.
  • Fuglseth E, Krane Tvedt TH, Hoff B. 2008b. Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones. Tetrahedron 64:7318–7323.
  • Gamble MP, Smith ARC, Wills M. 1998. A novel phosphinamide catalyst for the asymmetric reduction of ketones by borane. J Org Chem 63:6068–6071.
  • Goswami A, Goswami J. 2005. Corrigendum to DMSO-triggered enhancement of enantioselectivity in Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols. Tetrahedron Lett 46:4411–4413.
  • Goswami, A, Bezbaruah, RL, Goswami, J, Borthakur, N, Dey, D, Hazarika, AK. 2000. A convenient stereoselective synthesis of (R)-(-)-denopamine and (R)-(-)-salmeterol. Tetrahedron: Asymmetry 12:3343–3348.
  • Hagmann WK. 2008. The many roles for fluorine in medicinal chemistry. J Med Chem 51:4359–4369.
  • Hanefeldt U, Gardossi L, Magner E. 2009. Understanding enzyme immobilisation. Chem Soc Rev 38:453–468.
  • Hoff BH, Anthonsen T. 1999. Gas chromatographic enantiomer separation of C-3 and C-4 synthons: prediction of absolute configuration from elution order and enzymatic resolution. Chirality 11:760–767.
  • Jacobsen EE, Hoff BH, Anthonsen T. 2000. Enantiopure derivatives of 1,2-alkanediols: substrate requirements for lipase B from Candida antarctica. Chirality 12:654–659.
  • Kirk O, Christensen MW. 2002. Lipases from Candida antarctica: unique biocatalysts from a unique origin. Org Proc Res Dev 6: 446–451.
  • Kourist R, Gonzalez-Sabin J, Liz R, Rebolledo R. 2005. Kinetic resolution of 1-biaryl- and 1-(pyridylphenyl)alkan-1-ols catalyzed by the Lipase B from Candida antarctica. Adv Synth Catal 347:695–702.
  • Renaudet O, Reymond JL. 2004. Synthesis of ether oligomers. Org Lett 6:397–400.
  • Schmidt M, Barbayianni E, Fotakopoulou I, Hoehne M, Constantinou-Kokotou V, Bornscheuer UT, Kokotos G. 2005. Enzymatic removal of carboxyl protecting groups. 1. Cleavage of the tert-butyl moiety. J Org Chem 70:3737–3740.
  • Tjosås F, Anthonsen T, Jacobsen EE. 2008. Biocatalalytic resolution of saphenic acid. Substrate preferences for lipases A and B from Candida antarctica. ARKIVOK vi:81–90.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.