Multi-step synthesis strategies towards 1,2-amino alcohols with special emphasis on phenylpropanolamines

Journal of Molecular Catalysis B: Enzymatic

Volumn 114, Issue , 2015, Pages 65-71

  Sehl, Torsten ^a   Maugeri, Zaira ^a   Rother, Dörte ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

Asymmetric synthesis; cascade; Chemical, chemo enzymatic, enzymatic; Chiral vicinal amino alcohols; Multi step reactions

Indexed keywords

AMINO ALCOHOLS; CHEMICAL INDUSTRY; STEREOCHEMISTRY;

1 ,2-AMINO ALCOHOLS; ASYMMETRIC SYNTHESIS; BROAD APPLICATION; ENZYMATIC REACTION; MULTISTEP REACTIONS; PHENYLPROPANOLAMINE; SYNTHESIS STRATEGY; SYNTHETIC ROUTES;

SYNTHESIS (CHEMICAL);

EID: 84930220122     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2014.12.005     Document Type: Article

References (64)

1. D.J.C. Constable, P.J. Dunn, J.D. Hayler, G.R. Humphrey, J.J.L. Leazer, R.J. Linderman, K. Lorenz, J. Manley, B.A. Pearlman, A. Wells, A. Zaks, and T.Y. Zhang Green Chem. 9 2007 411 420
2. T.C. Nugent Chiral Amine Synthesis 1st ed. 2010 John WILEY-VCH Verlag GmbH & Co. KGaA
3. S.T.U. Borman Chem. Eng. News 70 1992 5
4. A. Richards, and R. McCague Chem. Ind. (Lond.) 1997 422 425
5. S.W. Smith Toxicol. Sci. 110 2009 4 30
6. S.C. Stinson Chem. Eng. News 70 1992 46 79
7. V. Law, C. Knox, Y. Djoumbou, T. Jewison, A.C. Guo, Y. Liu, A. Maciejewski, D. Arndt, M. Wilson, V. Neveu, A. Tang, G. Gabriel, C. Ly, S. Adamjee, Z.T. Dame, B. Han, Y. Zhou, and D.S. Wishart Nucleic Acids Res. 42 2014 1091 1097
8. T.J. Donohoe, C.K.A. Callens, A. Flores, A.R. Lacy, and A.H. Rathi Chem. Eur. J. 17 2011 58 76
9. S.C. Bergmeier Tetrahedron 56 2000 2561 2576
10. O.K. Karjalainen, and A.M.P. Koskinen Org. Biomol. Chem. 10 2012 4311 4326
11. D.J. Ager, I. Prakash, and D.R. Schaad Chem. Rev. 96 1996 835 876
12. A. Liese, K. Seelbach, and C. Wandrey Industrial Biotransformations 2006 John Wiley & Sons, Inc.
13. H. Gröger, Y. Asano, and O. May Introduction - principles and historical landmarks of enzyme catalysis in organic synthesis Enzyme Catalysis in Organic Synthesis 2012 Wiley-VCH Verlag GmbH & Co. KGaA 1 42
14. K. Faber Introduction and background information Biotransformations in Organic Chemistry 6th ed. 2011 Springer-Verlag 1 30
15. J. Wang, and W. Lu Chiral drugs via biocatalytical approaches Chiral Drugs 2011 John Wiley & Sons, Inc. 77 136
16. A. Schmid, J.S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, and B. Witholt Nature 409 2001 258 268
17. L. Keinicke, P. Fristrup, P.-O. Norrby, and R. Madsen J. Am. Chem. Soc. 127 2005 15756 15761
18. G. Hildebrandt, W. Klavehn, US 1956950 A (1930).
19. H. Yun, J. Kim, K. Kinnera, and B.G. Kim Biotechnol. Bioeng. 93 2006 391 395
20. H.C. Hailes, P.A. Dalby, G.J. Lye, and J.M. Ward J. Cheminform. 27 2009 28 31
21. J.L. Galman, D. Steadman, S. Bacon, P. Morris, M.E. Smith, J.M. Ward, P.A. Dalby, and H.C. Hailes Chem. Commun. 46 2010 7608 7610
22. C. Ingram, M. Bommer, M. Smith, P. Dalby, J. Ward, H. Hailes, and G. Lye Biotechnol. Bioeng. 96 2007 559 569
23. M.E. Smith, B.H. Chen, E.G. Hibbert, U. Kaulmann, K. Smithies, J.L. Galman, F. Baganz, P.A. Dalby, H.C. Hailes, and G.J. Lye Org. Process Res. Dev. 14 2009 99 107
24. J.M. Hagel, R. Krizevski, K. Kilpatrick, Y. Sitrit, F. Marsolais, E. Lewinsohn, and P.J. Facchini Genet. Mol. Biol. 34 2011 640 646
25. O. Wolfes Arch. Pharm. 268 1930 81 83
26. R. Krizevski, E. Bar, O. Shalit, A. Levy, J.M. Hagel, K. Kilpatrick, F. Marsolais, P.J. Facchini, S. Ben-Shabat, and Y. Sitrit Phytochemistry 81 2012 71 79
27. ® Healthcare Series Internet Database (Greenwood Village, CO) 2014 Thomson Healthcare
28. B.B. Hoffman, and R.J. Lefkowitz Catecholamines, sympathomimetic drugs and adrenergic receptor antagonists The Pharmacologial Basis of Therapeutics 1996 McGraw-Hill Companies, Inc. 222 224
29. L. Lasagna Phenylpropanolamine A Review 1st ed. 1988 John Wiley & Sons Inc.
30. J. Morgan Phenylpropanolamine A Critical Analysis of Reported Adverse Drug Reactions and Overdosage 1st ed. 1986 Jack K. Burgess Inc.
31. M. Weintraub Phenylpropanolamine as an anorexiant agent in weight control: a review of published and unpublished studies Phenylpropanolamine: Risks, Benefits and Controversies 5th ed. 1985 Greenwood Pub Group, Inc. 53 79
32. W.N. Kernan, C.M. Viscoli, L.M. Brass, J.P. Broderick, T. Brott, E. Feldmann, L.B. Morgenstern, J.L. Wilterdink, and R.I. Horwitz N. Engl. J. Med. 343 2000 1826 1832
33. Food and Drug Administration Phenylpropanolamine-Containing Drug Products for Over-the-Counter Human Use 2005 http://www.gpo.gov/fdsys/pkg/FR-2005-12-22/pdf/E5-7646.pdf
34. R. SoRelle Circulation 102 2000 E9041 E9043
35. B. Yoon, H. Bae, K. Hong, S. Lee, B. Park, K. Yu, M. Han, Y. Lee, D. Chung, and J. Park Neurology 68 2007 146 149
36. M. Yakoot J. Pharmacol. Pharmacother. 3 2012 4 6
37. EU Clinical Trials Register 2014 https://www.clinicaltrialsregister.eu/ctr-search/trial/2012-003426-24/DE
38. G. Laux, and O. Dietmaier Psychostimulanzien Psychopharmaka 2013 Springer-Verlag 189 195
39. L. Yan, Z. Diansong, S.S. Ferguson, P. Dorff, T.R. Simpson, and S.W. Grimm Xenobiotica 40 2010 721 729
40. D.G. Allen, N.M. Aston, N. Trivedi, C.D. Edlin, WO2004024728/A3 (2007).
41. Sigma-Aldrich Inc., http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Datasheet/c222dat.Par.0001.File.tmp/c222dat.pdf, (2012).
42. M.T. Reetz, M.W. Drewes, and A. Schmitz Angew. Chem. 99 1987 1186 1188
43. C. Kashima, T. Maruyama, Y. Fujioka, and K. Harada J. Chem. Soc. 1989 1041 1046
44. C. Kashima, T. Maruyama, K. Harada, S. Hibi, and Y. Omote J. Chem. Res. Synop. 1988 62 63
45. R. Bonar-Law, A. Davis, B. Dorgan, M. Reetz, and A. Wehrsig Tetrahedron Lett. 31 1990 6725 6728
46. R. Häner, B. Olano, and D. Seebach Helv. Chim. Acta 70 1987 1676 1693
47. G.-I. Hwang, J.-H. Chung, and W.K. Lee J. Org. Chem. 61 1996 6183 6188
48. Y. Lim, and W.K. Lee Tetrahedron Lett. 36 1995 8431 8434
49. D.A. Claremon, P.K. Lumma, and B.T. Phillips J. Am. Chem. Soc. 108 1986 8265 8266
50. D. Duveen, and J. Kenyon J. Chem. Soc. 1939 1697 1701
51. V.S. Martin, S.S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, and K.B. Sharpless J. Am. Chem. Soc. 103 1981 6237 6240
52. C.R. Noe, M. Knollmüller, G. Göstl, and P. Gärtner Monatsh. Chem. 122 1991 283 290
53. W. Oppolzer, O. Tamura, G. Sundarababu, and M. Signer J. Am. Chem. Soc. 114 1992 5900 5902
54. S. Minakata, M. Nishimura, T. Takahashi, Y. Oderaotoshi, and M. Komatsu Tetrahedron Lett. 42 2001 9019 9022
55. D.J. Kim, and B.T. Cho Bull. Korean Chem. Soc. 24 2003 1641 1648
56. H.-K. Lee, S. Kang, and E.B. Choi J. Org. Chem. 77 2012 5454 5460
57. T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, and H. Griengl Angew. Chem. Int. Ed. 45 2006 3454 3456
58. F. Effenberger, B. Hörsch, S. Förster, and T. Ziegler Tetrahedron Lett. 31 1990 1249 1252
59. F. Effenberger, B. Gutterer, and T. Ziegler Liebigs Ann. Chem. 3 1991 267 273
60. O.C. Kreutz, P.J.S. Moran, and J.A.R. Rodrigues Tetrahedron: Asymm. 8 1997 2649 2653
61. P. Moran, J. Rodrigues, I. Joekes, E. Brenelli, and R. Leite Biocatal. Biotransform. 9 1994 321 328
62. T. Sehl, H.C. Hailes, J.M. Ward, R. Wardenga, E. von Lieres, H. Offermann, R. Westphal, M. Pohl, and D. Rother Angew. Chem. Int. Ed. 52 2013 6772 6775
63. X. Wu, M. Fei, Y. Chen, Z. Wang, and Y. Chen Appl. Microbiol. Biotechnol. 98 2014 7399 7408
64. T. Sehl, H.C. Hailes, J.M. Ward, U. Menyes, M. Pohl, and D. Rother Green Chem. 16 2014 3341 3348