Bäckvall, J.-E. : 2023 Science of Synthesis, 2022/4: Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT) DOI: 10.1055/sos-SD-237-00100
Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

8 Chemoenzymatic Dynamic Kinetic Asymmetric Transformation

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Book

Editor: Bäckvall, J.-E.

Authors: Adriaensen, K. ; Akai, S. ; Berreur, J. ; Bhat, V. ; Clayden, J. ; Collins, B. S. L. ; Córdova, A. ; De Vos, D. ; Deiana, L.; Faber, K. ; Fletcher, S. P. ; Goetzke, F. W. ; González-Granda, S. ; Gotor-Fernández, V. ; Hafeman, N. J. ; Jin, Z. ; Kanomata, K. ; Kroutil, W. ; Liu, Y.; Modicom, F.; Pàmies, O. ; Sardini, Jr., S. R.; Stoltz, B. M. ; Winkler, C. K. ; Wu, X. ; Xie, J.-H. ; Zhang, K.; Zhou, Q.-L.

Title: Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

Print ISBN: 9783132453777; Online ISBN: 9783132453791; Book DOI: 10.1055/b000000439

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

The combination of enzymes and metal complexes can be used to achieve the de-epimerization of diastereoisomeric mixtures. Thus, by means of this chemoenzymatic dynamic kinetic asymmetric transformation (DYKAT), a wide range of racemic diols and, to a lesser extent, amino alcohols and diamines, have been transformed into a single diastereoisomer in excellent yields, and diastereo- and enantioselectivities.

 
  • 1 Pasteur L. Ann. Chim. Phys. 1848; 24: 442
  • 2 Vedejs E, Jure M. Angew. Chem. Int. Ed. 2005; 44: 3974
  • 3 Pellissier H. Tetrahedron 2008; 64: 1563
  • 4 Kim M.-J, Ahn Y, Park J. Curr. Opin. Biotechnol. 2002; 13: 578
  • 5 Pàmies O, Bäckvall J.-E. Chem. Rev. 2003; 103: 3247
  • 6 Martín-Matute B, Bäckvall J.-E. Curr. Opin. Chem. Biol. 2007; 11: 226
  • 7 Verho O, Bäckvall J.-E. J. Am. Chem. Soc. 2015; 137: 3996
  • 8 Larsson ALE, Persson BA, Bäckvall J.-E. Angew. Chem. Int. Ed. Engl. 1997; 36: 1211
  • 9 Paetzold J, Bäckvall J.-E. J. Am. Chem. Soc. 2005; 127: 17620
  • 10 Steinreiber J, Faber K, Griengl H. Chem.–Eur. J. 2008; 14: 8060
  • 11 Trost BM, Osipov M, Dong G. J. Am. Chem. Soc. 2010; 132: 15800
  • 12 Persson BA, Larsson ALE, Le Ray M, Bäckvall J.-E. J. Am. Chem. Soc. 1999; 121: 1645
  • 13 Persson BA, Huerta FF, Bäckvall J.-E. J. Org. Chem. 1999; 64: 5237
  • 14 Edin M, Bäckvall J.-E. J. Org. Chem. 2003; 68: 2216
  • 15 Martín-Matute B, Edin M, Bäckvall J.-E. Chem.–Eur. J. 2006; 12: 6053
  • 16 Borén L, Leijondahl K, Bäckvall J.-E. Tetrahedron Lett. 2009; 50: 3237
  • 17 Leijondahl K, Borén L, Braun R, Bäckvall J.-E. Org. Lett. 2008; 10: 2027
  • 18 Leijondahl K, Borén L, Braun R, Bäckvall J.-E. J. Org. Chem. 2009; 74: 1988
  • 19 Fransson A.-BL, Xu Y, Leijondahl K, Bäckvall J.-E. J. Org. Chem. 2006; 71: 6309
  • 20 Olofsson B, Bogár K, Fransson A.-BL, Bäckvall J.-E. J. Org. Chem. 2006; 71: 8256
  • 21 Krumlinde P, Bogár K, Bäckvall J.-E. Chem.–Eur. J. 2010; 16: 4031
  • 22 Ferreira EM, Stoltz BM. J. Am. Chem. Soc. 2001; 123: 7725
  • 23 Bøgesø KP, Christensen AV, Hyttel J, Liljefors T. J. Med. Chem. 1985; 28: 1817
  • 24 Veld MAJ, Hult K, Palmans ARA, Meijer EW. Eur. J. Org. Chem. 2007; 5416
  • 25 Edin M, Steinreiber J, Bäckvall J.-E. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5761
  • 26 Edin M, Martín-Matute B, Bäckvall J.-E. Tetrahedron: Asymmetry 2006; 17: 708
  • 27 Pàmies O, Bäckvall J.-E. J. Org. Chem. 2002; 67: 9006
  • 28 Fransson A.-BL, Borén L, Pàmies O, Bäckvall J.-E. J. Org. Chem. 2005; 70: 2582
  • 29 Solladié G, Huser N. Recl. Trav. Chim. Pays-Bas 1995; 114: 153
  • 30 Martín-Matute B, Bäckvall J.-E. J. Org. Chem. 2004; 69: 9191
  • 31 Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 7562
  • 32 Hilker S, Posevins D, Unelius CR, Bäckvall J.-E. Chem.–Eur. J. 2021; 27: 15623
  • 33 Millet R, Träff AM, Petrus ML, Bäckvall J.-E. J. Am. Chem. Soc. 2010; 132: 15182
  • 34 Lihammar R, Rönnols J, Widmalm G, Bäckvall J.-E. Chem.–Eur. J. 2014; 20: 14756