Dynamic kinetic resolution in the asymmetrie synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane

Chemistry - A European Journal

Volumn 14, Issue 27, 2008, Pages 8082-8085

  Malkov, Andrei V ^a,b   Stončius, Sigitas ^a   Vranková, Kvetoslava ^a   Arndt, Matthias ^a   Kočovský, Pavel ^a  

^a Technology and Innovation Centre   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Amino acids; Asymmetric synthesis; Imines; Organocatalysis; Reduction

Indexed keywords

AMINO ACIDS; CHEMICAL REACTIONS; HYDROSILYLATION; ORGANIC ACIDS;

ASYMMETRIC SYNTHESIS; IMINES; ORGANOCATALYSIS; REDUCTION;

AMINES;

AMIDE; AMINE; AMINO ACID; SILANE DERIVATIVE; TRICHLOROSILANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION; PH; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

AMIDES; AMINES; AMINO ACIDS; CATALYSIS; HYDROGEN-ION CONCENTRATION; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SILANES; STEREOISOMERISM; THERMODYNAMICS;

EID: 53849083142     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801244     Document Type: Article

References (54)

1. For an overview, see: D. L. Steer, R. A. Lew, P. Perlmutter, A. I. Smith, M.-I. Aguilar, Curr. Med. Chem. 2002, 9, 811-822.
2. For overviews, see: a) D. C. Cole, Tetrahedron 1994, 50, 9517-9582;
3. b) G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1999, 11-128;
4. c) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991 -8035;
5. d) H.-J. Drexler, J. You, S. Zhang, C. Fischer, W. Baumann, A. Spannenberg, D. Heller, Org. Process Res. Dev. 2003, 7, 355-361;
6. e) J.-A. Ma, Angew. Chem. 2003, 115, 4426-4435;
7. Angew. Chem. Int. Ed. 2003, 42, 4290-4299;
8. f) N. Sewald, Angew. Chem. 2003, 115, 5972-5973;
9. Angew. Chem. Int. Ed. 2003, 42, 5794-5795;
10. g) L. Gerald, D. Seebach. Biopolymers 2004, 76, 206-243;
11. h) D. Seebach, T. Kimmerlin, R. Sebesta, M. A. Campo, A. K. Beck, Tetrahedron 2004, 60, 7455-7506;
12. i) E. Juaristi, V. A. Soloshonok. Enantioselective Synthesis of β-Amino Acids, Wiley, Hoboken, 2005.
13. For the most recent examples of catalytic enantioselective protocols for Mannich reaction, see, for example: a) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764;
14. b) J. W. Yang, M. Stadler, B. List, Angew. Chem. 2007, 119, 615-617;
15. Angew. Chem. Int. Ed. 2007, 46, 609-611;
16. c) J. Vesely, R. Rios, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2007, 48, 421-425;
17. d)J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048-6049;
18. e) F. Tanaka, C. F. Barbas, J. Am. Chem. Soc. 2007, 129, 195-213; for the Reformatsky reaction, see:
19. f) P. G. Cozzi, Adv. Synth. Catal. 2006, 348, 2075-2079;
20. g) P. G. Cozzi, E. Rivalta, Angew. Chem. 2005, 117, 3666-3669;
21. Angew. Chem. Int. Ed. 2005, 44, 3600-3603.
22. a) J. Halpern, Science 1982, 217, 401; for an overview on asymmetric hydrogenation of functionalized alkenes, see:
23. b) J. M. Brown, Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 199-246.
24. a) S. Lee, Y. J. Zhang, Org. Lett. 2002, 4, 2429-2431;
25. b) W. Tang, X. Zhang, Org. Lett. 2002, 4, 4159-4161.
26. Y. Hsiao, N. R. Rivera, T. Rosner, S. W. Krska, E. Njolito, F. Wang, Y. Sun, J. D. Armstrong, E. J. J. Grabowski, R. D. Tillyer, F. Spindler, C. Malan, J. Am. Chem. Soc. 2004, 126, 9918-9919.
27. Q. Dai, W. Yang, X. Zhang, Org. Lett. 2005, 7, 5343-5345.
28. a) W. Tang, S. Wu, X. Zhang, J. Am. Chem. Soc. 2003, 125, 9570-9571;
29. b) J. Elaridi, A. Thaqi, A. Prosser, W. R. Jackson, A. J. Robinson, Tetrahedron: Asymmetry 2005, 16, 1309-1319.
30. a) A. V. Malkov, A. Mariani, K. N. MacDougall, P. Koečovský , Org. Lett. 2004, 6, 2253-2256;
31. b) A. V. Malkov, S. Stonečius, K. N. MacDougall, A. Mariani, G. D. McGeoch, P. Koečovský, Tetrahedron 2006, 62, 264-284;
32. c) A. V. Malkov, M. Figlus, S. Stonečius, P. Koeč ovský, J. Org. Chem. 2007, 72, 1315-1325.
33. For chiral pyridyloxazolines as catalysts in the reduction of both imines and ketones, see: A. V. Malkov, A. J. P. Stewart-Liddon. P. Ramírez-López, L. Bendová, D. Haigh, P. Koěovský, Angew. Chem. 2006, 118, 1460-1463;
34. Angew. Chem. Int. Ed. 2006, 45, 1432-1435.
35. For the asymmetric reduction of imines with trichlorosilane, see also: a) F. Iwasaki, O. Omonura, K. Mishima, T. Kanematsu, T. Maki, Y. Matsumura, Tetrahedron Lett. 2001, 42, 2525-2527;
36. b) O. Onomura, Y. Kouchi, F. Iwasaki, Y. Matsumura, Tetrahedron Lett. 2006, 47, 3751-3754;
37. c) Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun, Org. Lett. 2006, 8, 999-1001;
38. d) Z. Wang, M. Cheng, P. Wu, S. Wei, J. Sun, Org. Lett. 2006, 8, 3045-3048.
39. A. V. Malkov, S. Stoněius, P. Koěovský, Angew. Chem. 2007, 119, 3796-3798;
40. Angew. Chem. Int. Ed. 2007, 46, 3722-3724.
41. For a single example of asymmetric reduction of an enamine with low selectivity, see ref. [11b].
42. For leading reviews on DKR, see: a) R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-55;
43. b) R. S. Ward, Tetrahedron: Asymmetry 1995, 6, 1475-1490;
44. c) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321-331;
45. d) H. Pellissier, Tetrahedron 2003, 59, 8291-8327;
46. e) O. Párnies, J.-E. Bäckvall, Chem. Rev. 2003, 103, 3247-3262; for a recent example of asymmetric reductive amination by DKR. see:
47. f) S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13074-13075.
48. For the method, see: J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, P. L. Alsters, F. L. van Delft, F. P. J. T. Rutjes, Tetrahedron Lett. 2006, 47, 8109-8113.
49. N. Berova, B. J. Kurtev, Tetrahedron 1969, 25, 2301-2311.
50. a) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808;
51. Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
52. b) Y. Hayashi, T. Urushima, W. Tsuboi. M. Shoji, Nat. Protocols 2007, 2, 113-118.
53. 2-amino nitrile 7 in 30% ee.
54. V. V. R. Rao, C. Wentrup, J. Chem. Soc. Perkln Trans. 1 2002, 1232-1235.