Proline-catalyzed Mannich reaction of aldehydes with N-Boc-imines

Angewandte Chemie - International Edition

Volumn 46, Issue 4, 2007, Pages 609-611

  Yang, Jung Woon ^a   Stadler, Michael ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Amino aldehydes; Asymmetric synthesis; Imines; Mannich reaction; Organocatalysis

Indexed keywords

AMINO ALDEHYDES; DIASTEREOSELECTIVITY; ENANTIOSELECTIVITY; IMINES; MANNICH REACTIONS; ORGANOCATALYSIS;

AMINO ACIDS; CATALYSIS; NITROGEN COMPOUNDS; PRECIPITATION (CHEMICAL); REACTION KINETICS; STEREOCHEMISTRY;

ALDEHYDES;

ALDEHYDE; FORMIC ACID DERIVATIVE; IMINE; PROLINE; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY;

ALDEHYDES; CATALYSIS; FORMIC ACID ESTERS; IMINES; PROLINE;

EID: 33846550172     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603188     Document Type: Article

References (56)

1. For selected catalytic asymmetric Mannich reactions, see: a) H. Fujieda, M. Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061;
2. b) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
3. c) S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431-432;
4. d) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475;
5. e) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548-4549;
6. f) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085;
7. Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
8. g) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12 964-12 965;
9. h) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339;
10. i) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712-4713;
11. j) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367;
12. k) L. Bernardi, A. S. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583-2591;
13. l) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
14. m) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777-8785;
15. n) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
16. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
17. o) T. P. Yoon, E. N. Jacobsen, Angew. Chem. 2005, 117, 470-472;
18. Angew. Chem. Int. Ed. 2005, 44, 466-468;
19. p) Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem. 2005, 117, 1549-1553;
20. Angew. Chem. Int. Ed. 2005, 44, 1525-1529;
21. q) T. B. Poulsen, C. Alemparte, S. Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956-2959;
22. Angew. Chem. Int. Ed. 2005, 44, 2896-2899;
23. r) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439-4442;
24. Angew. Chem. Int. Ed. 2005, 44, 4365-4368;
25. s) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11 256-11 257;
26. t) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779;
27. u) J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048-6049;
28. v) A. Hasegawa, Y. Naganawa, M. Fushimi, K. Ishihara, H. Yamamoto, Org. Lett. 2006, 8, 3175-3178.
29. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
30. b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
31. c) P. Pojarliev, W. T. Biller, H. J. Martin, B. List, Synlett 2003, 1903-1905.
32. a) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
33. b) A Córdova, S.-i. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867;
34. c) W. Notz, F. Tanaka, S.-i. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634;
35. d) T. Ooi, M. Kameda, J.-i. Fujii, K. Maruoka, Org. Lett. 2004, 6, 2397-2399;
36. e) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558-560;
37. f) A. Córdova, Chem. Eur. J. 2004, 10, 1987-1997;
38. g) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. 2005, 117, 4147-4151;
39. Angew. Chem. Int. Ed. 2005, 44, 4079-4083;
40. h) B. Westermann, C. Neuhaus, Angew. Chem. 2005, 117, 4145-4147;
41. Angew. Chem. Int. Ed. 2005, 44, 4077-4079;
42. i) T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16 408-16 409;
43. j) W.-W. Liao, I. Ibrahem, A. Córdova, Chem. Commun. 2006, 674-676;
44. k) S. Mitsumori, H. Zhang, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 1040-1041;
45. l) I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760-1762.
46. After the completion of this manuscript, Enders et al. reported two examples of a proline-catalyzed Mannich reaction of a ketone (2,2-dimethyl-1,3-dioxan-5-one) with N-Boc imines 2a and 2g, see: a) D. Enders, M. Vrettou, Synthesis 2006, 2155-2158;
47. b) D. Enders, C. Grondai, M. Vrettou, Synthesis 2006, 3597-3604.
48. 2O); see: S. G. Davies, O. Ichihara, I. A. S. Walters, J. Chem. Soc. Perkin Trans. 1 1994, 1141-1147.
49. a) H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824-1839;
50. b) E. A. Porter, X. Wang, H.-S. Lee, B. Weisblum, S. H. Gellman, Nature 2000, 404, 565;
51. c) D. Seebach, A. Jacobi, M. Rueping, K. Gademann, M. Ernst, B. Jaun, Helv. Chim. Acta 2000, 83, 2115-2140.
52. For reviews on the asymmetric synthesis of β-amino acids, see: d) D. C. Cole, Tetrahedron 1994, 50, 9517-9582;
53. e) E. Juaristi, D. Quintana, J. Escalante, Aldrichimica Acta 1994, 27, 3-11;
54. f) G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117-128;
55. g) Enantioseleclive Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley, New York, 1997.
56. A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.