Highly Stereoselective Metal-Free Catalytic Reduction of Imines: An Easy Entry to Enantiomerically Pure Amines and Natural and Unnatural α-Amino Esters

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2928-2931

  Gulzzettl, Stefania ^a   Benaglia, Maurizio ^a   Rossi, Sergio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67649506347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900945h     Document Type: Article

References (54)

1. (a) Tararov, V. L.; Borner, A. Synlett 2005, 203.
2. (b) Blaser, H.-U.; Malan, C; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003,345, 103. For pertinent reviews, see also:
3. (c) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
4. (d) Vilaivan, T.; Bhanthumnavin, W.; Sritana-Anant, Y. Curr. Org. Chem. 2005, 9, 1315.
5. Constable, D. J. C; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, J. Green Chem. 2007, 9, 411.
6. Blaser, H.-U.; Pugin, B.; Spindler, F.; Thommen, M. Ace Chem. Res, 2007, 40, 1240,
7. and references cited thereinFor a special issue on hydrogenation and transfer hydrogenation, see: Krische, M. J.; Sun, Y. Acc. Chem. Res. 2007, 40, 12.
8. Reviews: (a) Dalko, P. L; Moisan, L. Angew Chem., Int. Ed. 2004, 43, 5138.
9. (b) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638. For reviews on supported organic catalysts, see:
10. (c) Puglisi, A.; Cozzi, F.; Benaglia, M. Chem. Rev. 2003, 103, 3401-3430.
11. (d) Cozzi, F. Adv. Synth. Catal. 2006, 344, 1267-1290.
12. (e) Benaglia, M. New J. Chem. 2006, 30, 1525-1533.
13. Anastas, P. T.; Warner, J. C Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
14. Reductive animation: for selected recent references for organometallic systems see ref 2 and:
15. (a) Reetz, M. T.; Bondarev, O. Angew. Chem., Int. Ed. 2007, 46, 4523.
16. (b) Graves, C. R.; Scheidt, K. A.; Nguyen, S. T. Qrg. Lett. 2006, 8, 1229. For organic catalysts, see:
17. (c) Ouellet, S. G.; Walji, A.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327.
18. (d) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
19. (e) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.
20. (f) Storer, R. L; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84. For a recent biocatalytic reductive animation, see:
21. (g) Koszelewski, D.; Lavandera, L; Clay, D.; Guebitz, G. M.; Rozzell, D.; Kroutil, W. Angew. Chem., Int. Ed. 2008, 47, 9337.
22. (h) Koszelewski, D.; Lavandera, L; Clay, D.; Rozzell, D.; Kroutil, W. Adv. Synth. Catal. 2008, 350, 2761.
23. See also: (i) Kadyrov, R.; Riermeier, T. H. Angew. Chem., Int. Ed. 2003, 43, 5472.
24. Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407.
25. Reviews: (a) Benaglia, M.; Guizzetti, S.; Pignataro, L. Coord. Chem. Rev. 2008, 252, 492.
26. (b) Denmark, S. E.; Beutner, G. L. Angew Chem., Int. Ed. 2008, 47, 1560.
27. Selected references: (a) Malkov, A. V.; Mariani, A.; MacDougal, K. N.; Koèovský, P. Org. Lett. 2004, 6, 2253.
28. (b) Malkov, A. V.; Stonèius, S.; Koèovský, P. Amgew. Chem., Int. Ed. 2007,46, 3722.
29. (c) Malkov, A. V.; Figlus, M.; Koèovsky, P. L. Org. Chem. 2008, 73, 3985.
30. (d) Matsumura, Y.; Ogura, K; Kouchi, Y.; Iwasaki, F.; Onomura, O. Org. Lett. 2006, 8, 3789.
31. (e) Wang, Z.; Ye, X.; Wei, S.; Wu, P.; Zhang, A.; Sun, J. Qrg. Lett. 2006, 8, 999.
32. (f) Pei, D.; Wang, Z.; Wei, S.; Zhang, Y.; Sun, J. Org. Lett. 2006, 8, 5913.
33. (g) Pei, D.; Zhang, Y.; Wei, S.; Wang, M.; Sun, J. Adv. Synth Catal. 2008, 350, 619.
34. (h) Wu, P.; Wang, Z.; Cheng, M.; Zhou, L.; Sun, J. Tetrahedron 2008, 64, 11304.
35. (i) Zheng, H.; Deng, J.; Lin, W.; Zhang, X. Tetrahedron Lett. 2007, 48, 7934.
36. (j) Gautier, R-M.; Jones, S.; Martin, S. J. Org. Biomol. Chem. 2009, 7, 229.
37. (m) For the first report where chiral amides were used as catalysts, see: Iwasaki, R; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett. 2001, 42, 2525.
38. Guizzetti, S.; Benaglia, M. European Patent Appl. Nov 30, 2007; PCT/EP/2008/010079, Nov 27, 2008.
39. Guizzetti, S., Benaglia, M. European Patent Appl. no. EP07023240.0, Sep 22, 2008.
40. Guizzetti, S.; Benaglia, M.; Cozzi, F.; Rossi, S.; Celentano, G. Chirality 2009, 21, 233.
41. For a review on the use of methylbenzylamine, see: Juaristi, E.; Leon-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441.
42. See: Alexakis, A.; Gille, S.; Prian, F.; Rosset, S.; Ditrich, K. Tetrahedron Lett. 2004, 45, 1449, and references cited therein.
43. Nugent, T. C; El-Shazly, M.; Wachaure, V. N. J. Org. Chem. 2008, 73, 1297,
44. and references cited thereinSee also: Adv. Synth. Catal. 2006, 10, 5433.
45. 1H NMR analysis on the crude reaction mixture and then confirmed after purification only one product was detected. HPLC analysis showed the presence of the other diastereoisomer to be <0.5%; see the Supporting Information. For a recent contribution on the analytical aspect, see: Claridge, T. D. W.; Davies, S. G. M.; Polywka, E. C.; Roberts, P. M.; Russell, A. J.; Savory, E. D.; Edward, D.; Smith, A. D. Org. Lett. 2008, 10, 5433.
46. 4 afforded the product with 78% diastereoselectivity.
47. 4.
48. For selective debenzylation reactions, see: Kanai, M.; Yasumoto, M.; Kuriyama, Y.; Inomiya, K.; Katsuhara, Y.; Higashiyama, K.; Ishii, A. Org. Lett. 2003, 5, 1007.
49. Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290.
50. Review: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
51. (b) Shang, G.; Yang, Q.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 6360.
52. See ref 8 and also: (a) Rueping, M.; Sugiono, E.; Azap, C; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
53. (b) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424.
54. Li, G.; Liang, Y.; Antilla, J. C J. Am. Chem. Soc. 2007,129, 5830.