Chemoenzymatic synthesis of boron-containing chiral amines and amides

Tetrahedron Asymmetry

Volumn 21, Issue 19, 2010, Pages 2419-2424

  Andrade, Leandro H ^a   Barcellos, Thiago ^a   Santiago, Carolina G ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; BORON; LIPASE B; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CANDIDA ANTARCTICA; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; KINETICS; PRIORITY JOURNAL;

EID: 78149283972     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.09.011     Document Type: Article

References (45)

1. For reviews concerning the Suzuki-Miyaura reaction, see: R. Martin, and S.L. Buchwald Acc. Chem. Res. 41 2008 1461 1473
2. F. Bellina, A. Carpita, and R. Rossi Synthesis 15 2004 2419 2440
3. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633 9695
4. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
5. Potassium organotrifluoroborates in palladium-catalyzed crosscoupling reactions: S. Darses, and J.-P. Genet Chem. Rev. 108 2008 288 325
6. G.A. Molander, and N. Ellis Acc. Chem. Res. 40 2007 275 286
7. G.A. Molander, and R. Figueroa Aldrichim. Acta 38 2005 49 56
8. H.A. Stefani, R. Cella, and A.S. Vieira Tetrahedron 63 2007 3623 3658
9. D.G. Hall Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine 2005 Wiley-VCH Weinheim, Germany
10. For boron compounds as proteasome inhibitors, see: H. Nakamura, M. Watanabe, H.S. Ban, W. Nabeyama, and A. Asai Bioorg. Med. Chem. Lett. 19 2009 3220 3224
11. L. Borissenko, and M. Groll Chem. Rev. 107 2007 687 717
12. B.D. Dorsey J. Med. Chem. 51 2008 1068 1072
13. W. Yang, X. Gao, and B. Wang Med. Chem. Res. 23 2003 346 368
14. S. Ebdrup, P. Jacobsen, A.D. Farrington, and P. Vedso Bioorg. Med. Chem. 13 2005 2305 2312
15. M.P. Raghavendra, and V. Prakash J. Agric. Food Chem. 50 2002 6037 6041
16. C.W. Garner J. Biol. Chem. 255 1980 5064 5068
17. C.P. Decicco, D.J. Nelson, Y. Luo, L. Shen, K.Y. Horiuchi, K.M. Amsler, L.A. Foster, S.M. Spitz, J.J. Merrill, C.F. Sizemore, K.C. Rogers, R.A. Copeland, and M.R. Harpel Bioorg. Med. Chem. Lett. 11 2001 2561 2564
18. R.F. Barth, J.A. Coderre, M.G. Vicente, and T.E. Blue Clin. Cancer Res. 11 2005 3987 4002
19. A.H. Soloway, W. Tjarks, B.A. Barnum, F.-G. Rong, R.F. Barth, I.M. Codogni, and J.G. Wilson Chem. Rev. 98 1998 1515 1562
20. T.C. Nugent Chiral Amine Synthesis: Methods, Developments and Applications 2010 Wiley-VCH Weinheim, Germany
21. For selected examples, see: A. L'Heureux, A. Martel, H. He, J. Chen, L.-Q. Sun, J.E. Starrett Jr., J. Natale, S.I. Dworetzky, R.J. Knox, D.G. Harden, D. Weaver, M.W. Thompson, and Y.-J. Wu Bioorg. Med. Chem. Lett. 15 2005 363 366
22. Wood, M. R., Anthony, N. J.; Bock, M. G.; Feng, D.-M.; Kuduk, S. D.; Su, D.-S.; Wai, J. M.-C. U.S. Patent 2003/0220375, November 27, 2003.
23. Leblanc, C.; Pulz, R. A.; Stiefl, N. J. U.S. Patent 2009/0181941, July 16, 2009.
24. S.D. Kuduk, C. Ng, D.-M. Feng, J.M.-C. Wai, R.S.L. Chang, C.M. Harrel, K.L. Murphy, R.W. Ramsom, D. Reiss, M. Ivarsson, G. Mason, S. Boyce, C. Tang, T. Prueksaritanont, R.M. Freidinger, D.J. Pettibone, and M.G. Bock J. Med. Chem. 47 2004 6439 6442
25. Claremon, D. A.; Zhuang, L.; Ye, Y.; Singh, S. B.; Tice, C. M.; Xu, Z.; Simpson, R. D. WO Patent 2009/088997, July 16, 2009.
26. Dyckman, A.; Pitts, W. J.; Belema, M.; Gill, P.; Kempson, J.; Qiu, Y.; Quesnelle, C.; Spergel, S. H.; Zusi, F. C. U.S. Patent 2006/106051, May 18, 2006.
27. L.H. Andrade, and T. Barcellos Org. Lett. 11 2009 3052 3055
28. For recent reviews concerning biocatalytic approaches to obtain optically active amines, see: Ref. 8
29. D. Koszelewski, K. Tauber, K. Faber, and W. Kroutil Trends Biotechnol. 28 2010 324 332
30. N.J. Turner Curr. Opin. Chem. Biol. 14 2010 115 121
31. V. Gotor-Fernandez, and V. Gotor Curr. Opin. Drug Disc. 12 2009 784 797
32. B. Miriyala, S. Bhattacharyya, and J.S. Williamson Tetrahedron 60 2004 1463 1471
33. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
34. A.J.J. Straathof, and J.A. Jongejan Enzyme Microb. Technol. 21 1997 559 571
35. F. Van Rantwijk, and R.A. Sheldon Tetrahedron 60 2004 501 519
36. H. Ismail, R.M. Lau, F. van Rantwijk, and R.A. Sheldon Adv. Synth. Catal. 350 2008 1511 1516
37. J.-H. Sun, R.-J. Dai, W.-W. Meng, and Y.-L. Deng Catal. Commun. 11 2010 987 991
38. M. Cammenberg, K. Hult, and S. Park ChemBioChem 7 2006 1745 1749
39. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keeler, R. Stürmer, and T. Zelinski Angew. Chem., Int. Ed. 43 2004 788 824
40. K. Han, J. Park, and M.-J. Kim J. Org. Chem. 73 2008 4302 4304
41. M. Rodríguez-Mata, E. García-Urdiales, V. Gotor-Fernández, and V. Gotor Adv. Synth. Catal. 352 2010 395 406
42. H. Wu, and J.J. Hynes Jr. Org. Lett. 12 2010 1192 1195
43. Y. Liu, and K. Ding J. Am. Chem. Soc. 127 2005 10488 10489
44. R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, and L.A. Cuccia J. Org. Chem. 56 1991 2656 2665
45. B. Wrackmeyer Prog. Nucl. Magn. Reson. Spectrosc. 12 1979 227