Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis

ChemCatChem

Volumn 9, Issue 4, 2017, Pages 555-558

  Uthoff, Florian ^a   Sato, Hirofumi ^a   Gröger, Harald ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

amines; asymmetric synthesis; compartmentation; hydroamination; transamination

Indexed keywords

AMINES; HYDROCARBONS; STYRENE;

ACTIVATED ALKENES; ASYMMETRIC SYNTHESIS; CATALYTIC SYSTEM; COMPARTMENTATION; HYDROAMINATIONS; ONE-POT SYNTHESIS; SYNTHETIC METHODS; TRANSAMINATION;

ENANTIOSELECTIVITY;

EID: 85013287777     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201601463     Document Type: Article

References (40)

1. A. Kleemann, J. Engels, B. Kutscher, D. Reichert, Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed., Thieme, Stuttgart, 2000.
2. Industrial Biotransformations, 2nd ed. (Eds.: A. Liese, K. Seelbach, C. Wandrey), Wiley-VCH, Weinheim, 2006.
3. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem. Int. Ed. 2004, 43, 788–824;
4. Angew. Chem. 2004, 116, 806–843.
5. C. K. Savile, J. M. Janey, E. C. Mundorff, J. C. Moore, S. Tam, W. R. Jarvis, J. C. Colbeck, A. Krebber, F. J. Fleitz, J. Brands, et al., Science 2010, 329, 305–309.
6. H.-U. Blaser, Adv. Synth. Catal. 2002, 344, 17–31.
7. Reviews:
8. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795–3892;
9. L. Huang, M. Arndt, K. Gooßen, H. Heydt, L. J. Gooßen, Chem. Rev. 2015, 115, 2596–2697;
10. M. T. Pirnot, Y.-M. Wang, S. L. Buchwald, Angew. Chem. Int. Ed. 2016, 55, 48–57;
11. Angew. Chem. 2016, 128, 48–57.
12. M. A. Giardello, V. P. Conticello, L. Brard, M. R. Gagne, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241–10254.
13. D. V. Gribkov, K. C. Hultzsch, F. Hampel, J. Am. Chem. Soc. 2006, 128, 3748–3759;
14. A. L. Reznichenko, T. J. Emge, S. Audörsch, E. G. Klauber, K. C. Hultzsch, B. Schmidt, Organometallics 2011, 30, 921–924;
15. X. Zhang, T. J. Emge, K. C. Hultzsch, Angew. Chem. Int. Ed. 2012, 51, 394–398;
16. Angew. Chem. 2012, 124, 406–410;
17. A. L. Reznichenko, K. C. Hultzsch, J. Am. Chem. Soc. 2012, 134, 3300–3311.
18. A. Hu, M. Ogasawara, T. Sakamoto, A. Okada, K. Nakajima, T. Takahashi, W. Lin, Adv. Synth. Catal. 2006, 348, 2051–2056;
19. M. C. Wood, D. C. Leitch, C. S. Yeung, J. A. Kozak, L. L. Schafer, Angew. Chem. Int. Ed. 2007, 46, 354–358;
20. Angew. Chem. 2007, 119, 358–362;
21. Y. Yang, S.-L. Shi, D. Niu, P. Liu, S. L. Buchwald, Science 2015, 349, 62–66;
22. Y. Xi, T. W. Butcher, J. Zhang, J. F. Hartwig, Angew. Chem. Int. Ed. 2016, 55, 776–780;
23. Angew. Chem. 2016, 128, 786–790.
24. H. Sato, W. Hummel, H. Gröger, Angew. Chem. Int. Ed. 2015, 54, 4488–4492;
25. Angew. Chem. 2015, 127, 4570–4574.
26. Independently of this work, recently a related catalytic system was reported for the preparation of primary amines as racemates. However, in spite of the combination of chemo- and biocatalyst this system is based on an exclusive combination of chemocatalysts (for Wacker-oxidation and non-asymmetric reductive amination via hydrogenation) and gives the amine products in racemic form: Y. Yang, N. I. Wong, P. Teo, Eur. J. Org. Chem. 2015, 1207–1210.
27. Review on enzymatic transamination: M. Höhne, U. T. Bornscheuer in Enzyme Catalysis in Organic Synthesis, Vol. 2, 3rd ed. (Eds.: K. Drauz, H. Gröger, O. May), Wiley-VCH, Weinheim, 2012, p. 779–820.
28. M. T. Mwangi, M. B. Runge, K. M. Hoak, M. D. Schulz, N. B. Bowden, Chem. Eur. J. 2008, 14, 6780–6788;
29. M. B. Runge, M. T. Mwangi, A. L. Miller, M. Perring, N. B. Bowden, Angew. Chem. Int. Ed. 2008, 47, 935–939;
30. Angew. Chem. 2008, 120, 949–953;
31. A. L. Miller, N. B. Bowden, J. Org. Chem. 2009, 74, 4834–4840.
32. B. Winblad, J. Cummings, N. Andreasen, G. Grossberg, M. Onofrj, C. Sadowsky, S. Zechner, J. Nagel, R. Lane, Int. J. Geriatr. Psychiatry 2007, 22, 456–467.
33. For previously developed chemoenzymatic syntheses of Rivastigmine, see:
34. J. Mangas-Sánchez, M. Rodríguez-Mata, E. Busto, V. Gotor-Fernández, V. Gotor, J. Org. Chem. 2009, 74, 5304–5310;
35. M. Fuchs, D. Koszelewski, K. Tauber, J. Sattler, W. Banko, A. K. Holzer, M. Pickl, W. Kroutil, K. Faber, Tetrahedron 2012, 68, 7691–7694;
36. M. Fuchs, D. Koszelewski, K. Tauber, W. Kroutil, K. Faber, Chem. Commun. 2010, 46, 5500–5502.
37. For reviews on the realization of novel “process windows” through reaction- and reactor-design as well as their importance for industrial processes, see:
38. Novel Process Windows: Innovative Gates to Intensified and Sustainable Chemical Processes (Eds.: V. Hessel, D. Kralisch, N. Kockmann), Wiley-VCH, Weinheim, 2015;
39. V. Hessel, D. Kralisch, N. Kockmann, T. Noël, Q. Wang, ChemSusChem 2013, 6, 746–789;
40. V. Hessel, Chem. Eng. Technol. 2009, 32, 1655–1681.