A highly enantioselective organocatalytic method for reduction of aromatic N-alkyl ketimines

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8789-8792

  Wang, Chao ^a   Wu, Xinjun ^a,b   Zhou, Li ^a   Sun, Jian ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amines; Asymmetric catalysis; Lewis bases; Organocatalysis; Reduction

Indexed keywords

ALKYLATION; AMINES; AROMATIC COMPOUNDS; CHIRALITY; ENANTIOMERS; ENANTIOSELECTIVITY; ORGANIC COMPOUNDS; REACTION KINETICS; STEREOCHEMISTRY;

ASYMMETRIC CATALYSIS; ASYMMETRIC INDUCTIONS; CARBOXAMIDE; CATALYST SYSTEMS; ENANTIOSELECTIVE; ENANTIOSELECTIVE ORGANOCATALYTIC METHODS; HIGH YIELDS; KETIMINES; LEWIS BASES; LEWIS BASEST; MILD CONDITIONS; ORGANOCATALYSIS; ORGANOCATALYST; SULFINAMIDE; TRICHLOROSILANE;

CATALYSIS;

DRUG DERIVATIVE; IMIPRAMINE; KETIPRAMINE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALKYLATION; CATALYSIS; IMIPRAMINE; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PHENOMENA; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 55049095134     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801479     Document Type: Article

References (46)

1. a) H.-U. Blaser, F. Spindler in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 247-265;
2. b) T. Okhuma, R. Noyori in Comprehensive Asymmetric Catalysis, Suppl. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 2004, pp. 43-53.
3. For recent reviews, see: a) V. I. Tararov, A. Borner, Synlett 2005, 203;
4. b) O. Riant, N. Mostefai, J. Courmarcel, Synthesis 2004, 2943;
5. c) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
6. d) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103.
7. For selected recent examples of transition metal catalyzed asymmetric reduction of imines, see: a) Y. Wang. S. Lu, Y.-G. Zhou, J. Org. Chem. 2007, 72, 3729;
8. b) M. T. Reetz, O. Bondarev, Angew. Chem. 2007, 119, 4607;
9. Angew. Chem. Int. Ed. 2007, 46, 4523;
10. c) Q. Yang, G. Shang, W. Gao, J. G. Deng, X. Zhang, Angew. Chem. 2006, 118, 3916;
11. Angew. Chem. Int. Ed. 2006, 45, 3832;
12. d) S. Zhu, J. Xie, Y. Zhang, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 12886.
13. For reviews, see: a) S. G. Quellet, A. M. Walji, W. C. MacMillan, Acc. Chem. Res. 2007, 40, 1327;
14. b) S.-L. You, Chem. Asian J. 2007, 2, 820; For examples, see:
15. c) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
16. d) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590;
17. Angew. Chem. Int. Ed. 2005, 44, 7424;
18. e) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
19. f) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 6903;
20. Angew. Chem. Int. Ed. 2006, 45, 6751;
21. g) G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830;
22. h) Q. Kang, Z.-A. Zhao, S.-L. You, Adv. Synth. Catal. 2007, 349, 1657;
23. i) M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001;
24. j) Q. Kang, Z. Zhao, S.-L. You, Org. Lett. 2008, 10, 2031.
25. a) F. Iwasaki, O. Onomura, K. Mishima, T. Kanematsu, T. Maki, Y. Matsumura, Tetrahedron Lett. 2001, 42, 2525;
26. b) O. Onomura. Y. Kouchi, F. Iwasaki, Y. Matsumura, Tetrahedron Lett. 2006, 47, 3751.
27. a) A. V. Malkov, A. Mariani, K. N. MacDougall, P. Kocovsky, Org. Lett. 2004, 6, 2253;
28. b) A. V. Malkov, S. Stoncius, K. N. MacDougall, A. Mariani, G. D. McGeoch, P. Kocovsky, Tetrahedron 2006, 62, 264;
29. c) A. V. Malkov, A. Liddon, P. Ramirez-Lopez, L. Bendova, D. Haigh, P. Kocovsky, Angew. Chem. 2006, 118, 1460;
30. Angew. Chem. Int. Ed. 2006, 45, 1432;
31. d) A. V. Malkov, M. Figlus, S. Stoncius, P. Kocovsky, J. Org. Chem. 2007, 72, 1315;
32. e) A. V. Malkov, S. Stoncius, P. Kocovsky, Angew. Chem. 2007, 119, 3796;
33. Angew. Chem. Int. Ed. 2007, 46, 3722.
34. a) Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun, Org. Lett. 2006, 8, 999;
35. b) Z. Wang, M. Cheng, P. Wu, S. Wei, J. Sun, Org. Lett. 2006, 8, 3045;
36. c) Z. Wang, S. Wei, C. Wang, J. Sun, Tetrahedron: Asymmetry 2007, 18, 705;
37. d) L. Zhou, Z. Wang, S. Wei, J. Sun, Chem. Commun. 2007, 2977;
38. e) D. Pei, Z. Wang, Y. Zhang, S. Wei, J. Sun, Org. Lett. 2006, 8, 5913;
39. f) D. Pei, Y. Zhang, S. Wei, M. Wang, J. Sun, Adv. Synth. Catal., 2008, 350, 619.
40. a) C. Baudequin, D. Chaturvedi, S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 2623;
41. b) H. Zheng, J. Deng, W. Lin, X. Zhang, Tetrahedron Lett. 2007, 48, 7934.
42. CCDC 685373 for 5a and 685374 for 4a contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
43. There have been extremely rare examples of transition metal catalysts reported in the literature that are applicable for the highly enantioselective reduction of various N-alkyl ketimines, see: a) X. Verdaguer, U. Lange, S. L. Buchwald, Angew. Chem. 1998, 110, 1174;
44. Angew. Chem. Int. Ed. 1998, 37, 1103;
45. b) X. Verdaguer, U. Lange, M. T. Reding, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 6784.
46. Similar phenomena have been observed by us and others before, see ref. [7a,b], and [10a].