Chemoenzymatic synthesis of all four diastereomers of 2,6-disubstituted piperidines through stereoselective monoamination of 1,5-diketones

Chemistry - A European Journal

Volumn 19, Issue 8, 2013, Pages 2859-2865

  Simon, Robert C ^a   Zepeck, Ferdinand ^b   Kroutil, Wolfgang ^c  

^a AUSTRIAN CENTRE OF INDUSTRIAL BIOTECHNOLOGY   (Austria)

^b NOVARTIS PHARMA AG   (Switzerland)

^c Institute of Chemistry   (Austria)

Author keywords

transaminases; alkaloids; chiral amines; piperidines; regioselectivity

Indexed keywords

CHEMO-ENZYMATIC SYNTHESIS; CHIRAL AMINES; CONFORMATIONAL CHANGE; DIASTEREOMERS; ENANTIO; LEWIS ACID; PIPERIDINES; RING CLOSURES; STEREO-SELECTIVE;

ALKALOIDS; METABOLITES; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; REGIOSELECTIVITY; SCAFFOLDS; STEREOSELECTIVITY;

KETONES;

ALKALOID; AMINOTRANSFERASE; KETONE; LEWIS ACID; PIPERIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMINATION; KETONES; LEWIS ACIDS; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM; TRANSAMINASES;

EID: 84873653146     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202793     Document Type: Article

References (97)

1. A. Kirschning, F. Hahn, Angew. Chem. 2012, 124, 4086-4096
2. Angew. Chem. Int. Ed. 2012, 51, 4012-4022
3. V. Resch, J. H. Schrittwieser, E. Siirola, W. Kroutil, Curr. Opin. Biotechnol. 2011, 22, 793-799
4. T. Fischer, J. Pietruszka, Top. Curr. Chem. 2010, 297, 1-43
5. R. N. Patel, ACS Catal. 2011, 1, 1056-1074
6. R. N. Patel, Coord. Chem. Rev. 2008, 252, 659-701.
7. K. Faber, Biotransformations in Organic Chemistry, 7th ed., Springer, Berlin, 2011
8. P. Grunwald, Biocatalysis: Biochemical Fundamentals and Applications, Imperial College Press, London, 2009
9. Modern Biocatalysis (Eds.:, W.-D. Fessner, T. Anthonsen,), Wiley-VCH, Weinheim, 2009
10. Asymmetric Organic Synthesis with Enzymes (Eds.:, V. Gotor, I. Alfonso, E. García-Uridales,), Wiley-VCH, Weinheim, 2008
11. U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis: Regio and Stereoselective Biotransformations, 2nd ed., Wiley-VCH, Weinheim, 2006
12. Biocatalysis in the Pharmaceutical and Biotechnology Industries (Ed.:, R. N. Patel,), CRC, Boca Raton, 2006
13. A. S. Bommarius, B. R. Riebel-Bommarius, Biocatalysis, Wiley-VCH, Weinheim, 2004.
14. M. Höhne, U. T. Bornscheuer, ChemCatChem 2009, 1, 42-51.
15. E. Busto, V. Gotor-Fernández, V. Gotor, Chem. Rev. 2011, 111, 3998-4035.
16. R. Carr, M. Alexeeva, A. Enright, T. S. C. Eve, M. J. Dawson, N. J. Turner, Angew. Chem. 2003, 115, 4955-4958
17. Angew. Chem. Int. Ed. 2003, 42, 4807-4810
18. C. J. Dunsmore, R. Carr, T. Fleming, N. J. Turner, J. Am. Chem. Soc. 2006, 128, 2224-2226
19. V. Köhler, K. R. Bailey, A. Znabet, J. Raftery, M. Helliwell, N. J. Turner, Angew. Chem. 2010, 122, 2228-2230
20. Angew. Chem. Int. Ed. 2010, 49, 2182-2184
21. T. Li, J. Liang, A. Ambrogelly, T. Brennan, G. Gloor, G. Huisman, J. Lalonde, A. Lekhal, B. Mijts, S. Muley, L. Newman, M. Tobin, G. Wong, A. Zaks, X. Zhang, J. Am. Chem. Soc. 2012, 134, 6467-6472.
22. S. Mathew, H. Yun, ACS Catal. 2012, 2, 993-1001
23. P. Tufvesson, J. Lima-Ramos, J. S. Jensen, N. Al-Haque, W. Neto, J. M. Woodley, Biotechnol. Bioeng. 2011, 108, 1479-1493
24. D. Koszelewski, K. Tauber, K. Faber, W. Kroutil, Trends Biotechnol. 2010, 28, 324-332
25. N. J. Turner, M. Truppo, in Chiral Amine Synthesis: Methods, Developments and Applications (Ed.:, T. C. Nugent,), Wiley-VCH, Weinheim, 2010, pp. 431-459
26. H. C. Hailes, P. A. Dalby, G. J. Lye, F. Baganz, M. Micheletti, N. Szita, J. M. Ward, Curr. Org. Chem. 2010, 14, 1883-1893
27. J. Ward, R. Wohlgemuth, Curr. Org. Chem. 2010, 14, 1914-1927.
28. F. G. Mutti, C. S. Fuchs, D. Pressnitz, N. G. Turrini, J. H. Sattler, A. Lerchner, A. Skerra, W. Kroutil, Eur. J. Org. Chem. 2012, 1003-1007
29. F. G. Mutti, C. S. Fuchs, D. Pressnitz, J. H. Sattler, W. Kroutil, Adv. Synth. Catal. 2011, 353, 3227-3233
30. S. Schätzle, F. Steffen-Munsberg, A. Thontowi, M. Höhne, K. Robins, U. Bornscheuer, Adv. Synth. Catal. 2011, 353, 2439-2445
31. M. D. Truppo, J. D. Rozzell, N. J. Turner, Org. Process Res. Dev. 2010, 14, 234-237
32. M. Höhne, S. Schätzle, H. Jochens, K. Robins, U. T. Bornscheuer, Nat. Chem. Biol. 2010, 6, 807-813
33. M. Fuchs, D. Koszelewski, K. Tauber, W. Kroutil, K. Faber, Chem. Commun. 2010, 46, 5500-5502
34. D. Koszelewski, M. Göritzer, D. Clay, B. Seisser, W. Kroutil, ChemCatChem 2010, 2, 73-77
35. C. K. Savile, J. M. Janey, E. C. Mundorff, J. C. Moore, S. Tam, W. R. Javis, J. C. Colbeck, A. Krebber, F. J. Fleitz, J. Brands, P. N. Devine, G. W. Huisman, G. J. Hughes, Science 2010, 329, 305-309
36. K. E. Cassimjee, C. Branneby, V. Abedi, A. Wells, P. Berglund, Chem. Commun. 2010, 46, 5569-5571
37. D. Koszelewski, I. Lavandera, D. Clay, G. M. Guebitz, D. Rozzell, W. Kroutil, Angew. Chem. 2008, 120, 9477-9480
38. Angew. Chem. Int. Ed. 2008, 47, 9337-9340
39. D. Koszelewski, I. Lavandera, D. Clay, D. Rozzell, W. Kroutil, Adv. Synth. Catal. 2008, 350, 2761-2767
40. J.-S. Shin, B.-G. Kim, Biotechnol. Bioeng. 1999, 65, 206-211.
41. B.-K. Cho, H.-Y. Park, J.-H. Seo, J. Kim, T.-J. Kang, B.-S. Lee, B.-G. Kim, Biotechnol. Bioeng. 2008, 99, 275-284
42. H.-S. Bea, H.-J. Park, S.-H. Lee, H. Yun, Chem. Commun. 2011, 47, 5894-5896
43. M. D. Truppo, N. J. Turner, J. D. Rozzell, Chem. Commun. 2009, 2127-2129
44. R. L. Hanson, B. L. Davis, S. L. Goldberg, R. M. Johnston, W. L. Parker, T. P. Tully, M. A. Montana, R. N. Patel, Org. Process Res. Dev. 2008, 12, 1119-1129
45. R. L. Hanson, B. L. Davis, Y. Chen, S. L. Goldberg, W. L. Parker, T. P. Tully, M. A. Montana, R. N. Patel, Adv. Synth. Catal. 2008, 350, 1367-1375.
46. R. C. Simon, B. Grischek, A. Steinreiber, F. Zepeck, F. Belaj, W. Kroutil, Angew. Chem. 2012, 124, 6817-6820
47. Angew. Chem. Int. Ed. 2012, 51, 6713-6716.
48. B. Haag, M. Mosrin, H. Ila, V. Malakhov, P. Knochel, Angew. Chem. 2011, 123, 9968-9999
49. Angew. Chem. Int. Ed. 2011, 50, 9794-9824
50. S. Fustero, M. Sánchez-Rosellõ, P. Barrio, A. Simõn-Fuentes, Chem. Rev. 2011, 111, 6984-7034; for enzymatic acylation, see
51. J. González-Sabín, R. Morán-Ramallal, F. Rebolledo, Chem. Soc. Rev. 2011, 40, 5321-5335; for enzymatic redox reactions, see
52. D. Monti, G. Ottolina, G. Carrea, S. Riva, Chem. Rev. 2011, 111, 4111-4140; for ring opening of aziridines, see
53. P. Lu, Tetrahedron 2010, 66, 2549-2560; for functionalization of alkenes and alkynes, see
54. M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. 2004, 116, 3448-3479
55. Angew. Chem. Int. Ed. 2004, 43, 3368-3398; for a recent example of enzymatic regioselective hydroxylation, see
56. S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nat. Chem. 2011, 3, 738-743.
57. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205.
58. V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471-13480
59. Q. Zhou, X. Chen, D. Ma, Angew. Chem. 2010, 122, 3591-3594
60. Angew. Chem. Int. Ed. 2010, 49, 3513-3516
61. Z. Gu, A, Zakarian, Angew. Chem. 2010, 122, 9896-9899
62. Angew. Chem. Int. Ed. 2010, 49, 9702-9705
63. P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404-408.
64. M. Ochiai, K. Miyamoto, T. Kaneaki, S. Hayashi, W. Nakanishi, Science 2011, 332, 448-451.
65. J. S. Arnold, G. T. Cizio, H. M. Nguyen, Org. Lett. 2011, 13, 5576-5579
66. J. S. Arnold, R. F. Stone, H. M. Nguyen, Org. Lett. 2010, 12, 4580-4583.
67. X.-Y. Liu, P. Gao, Y.-Q. Shen, Y.-M. Liang, Org. Lett. 2011, 13, 4196-4199.
68. R. W. Bates, K. Sa-Ei, Tetrahedron 2002, 58, 5957-5978.
69. M. G. P. Buffat, Tetrahedron 2004, 60, 1701-1729.
70. U. Kaulmann, K. Smithies, M. E. B. Smith, H. C. Hailes, H. M. Ward, Enzyme Microb. Technol. 2007, 41, 628-637
71. N. Ito, S. Kawano, J. Hagesawa, Y. Yasohara, Biosci. Biotechnol. Biochem. 2011, 75, 2093-2095
72. B.-Y. Hwang, B.-K. Cho, H. Yun, K. Koteshwar, B.-G. Kim, J. Mol. Catal. B 2005, 37, 47-55
73. V. Sieber, K. Grammann, B. Rühmann, T. Haas, J. Pfeffer, K. Doderer, C. Collmann, A. Skerra, C. Rausch, A. Lerchner, (Degussa Evonik GmbH, Essen), WO-Patent 2010/089171 A2, 2010
74. S. Kawano, N. Ito, Y. Yosohara, (Kaneka Corporation, Osaka), European Patent, EP2022852 A1, 2007.
75. K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, H. Yamamoto, J. Am. Chem. Soc. 1983, 105, 2831-2843
76. K. Maruoka, H. Yamamoto, Angew. Chem. 1985, 97, 670-683
77. Angew. Chem. Int. Ed. Engl. 1985, 24, 668-682.
78. M. Kavala, F. Mathia, H. Kožišek, P. Szolcsanyi, J. Nat. Prod. 2011, 74, 803-811
79. J. C. Gonzalez-Gomez, F. Foubelo, M. Yus, Synlett 2008, 2777-2780
80. I. Abrunhosa-Thomas, O. Roy, M. Barra, T. Besset, P. Chalard, Y. Troin, Synlett 2007, 1613-1615
81. C. Eriksson, K. Sjodin, F. Schlyter, H.-E. Hogberg, Tetrahedron: Asymmetry 2006, 17, 1074-1080
82. X. Wang, Y. Dong, J. Sun, X. Xu, R. Li, Y. Hu, J. Org. Chem. 2005, 70, 1897-1900
83. S. Yamauchi, S. Mori, Y. Hirai, Y. Kinoshita, Biosci. Biotechnol. Biochem. 2004, 68, 676-684
84. T. J. Wilkinson, N. W. Stehle, P. Beak, Org. Lett. 2000, 2, 155-158
85. S. Ciblat, P. Besse, V. Papastergiou, H. Beschambre, J.-L. Canet, Y. Troin, Tetrahedron: Asymmetry 2000, 11, 2221-2229
86. A. R. Katritzky, G. Yiu, B. Yang, P. J. Steel, J. Org. Chem. 1998, 63, 6699-6703
87. R. Chênevert, M. Dickman, J. Org. Chem. 1996, 61, 3332-3341
88. E. Lee, T. S. Kang, B. J. Joo, J. S. Tae, K. S. Li, C. K. Chung, Tetrahedron Lett. 1995, 36, 417-420
89. H. Takahata, H. Bandoh, M. Hanayama, T. Momose, Tetrahedron: Asymmetry 1992, 3, 607-608
90. L. Guerrier, J. Royer, D. S. Grierson, H.-P. Husson, J. Am. Chem. Soc. 1983, 105, 7754-7755.
91. M. J. Schneider, J. A. Montali, D. Hazen, C. E. Stanton, J. Nat. Prod. 1991, 54, 905-909
92. J. N. Tawara, A. Blokhin, T. A. Foderaro, F. R. Stermitz, J. Org. Chem. 1993, 58, 4813-4818.
93. E. Airiau, N. Girard, M. Pizzeti, J. Salvadori, M. Taddei, A. Mann, J. Org. Chem. 2010, 75, 8670-5673
94. C. Quinet, A. Ates, I. E. Marko, Tetrahedron Lett. 2008, 49, 5032-5035
95. A. P. Dobbs, S. J. J. Guesne, Synlett 2005, 2101-2103
96. D. M. Ryckman, R. V. Stevens, J. Org. Chem. 1987, 52, 4274-4279
97. R. K. Hill, T. Yuri, Tetrahedron 1977, 33, 1569-1571.