Catalytic asymmetric addition of β-ketoesters to various imines by using chiral palladium complexes

Angewandte Chemie - International Edition

Volumn 44, Issue 10, 2005, Pages 1525-1529

  Hamashima, Yoshitaka ^a   Sasamoto, Naoki ^a   Hotta, Daido ^a   Somei, Hidenori ^a   Umebayashi, Natsuko ^a   Sodeoka, Mikiko ^a  

^a NONE

Author keywords

Asymmetric catalysis; Enolates; Mannich reaction; Palladium; Schiff bases

Indexed keywords

ALDEHYDES; CARBOXYLIC ACIDS; CATALYST ACTIVITY; REACTION KINETICS;

ENANTIOSELECTIVITY; GLYOXYLATE; IMINES; KETOESTERS;

PALLADIUM COMPOUNDS;

3 CHLOROANILINE; ANILINE DERIVATIVE; BETA OXOCARBOXYLIC ACID ESTER; CARBONYL DERIVATIVE; ESTER; ETHYL GLYOXYLATE; GLYOXYLIC ACID DERIVATIVE; IMINE; N,N DIMETHYLFORMAMIDE; PALLADIUM COMPLEX; TETRAHYDROFURAN; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; MANNICH REACTION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 16244364063     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462202     Document Type: Article

References (64)

1. a) E. F. Kleinman in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 4.1;
2. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122; Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
3. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122; Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
4. For the synthesis of β-amino acids: a) Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley, New York, 1997;
5. b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
6. c) P. A. Magriotis, Angew. Chem. 2001, 113, 4507-4509; Angew. Chem. Int. Ed. 2001, 40, 4377-4379;
7. c) P. A. Magriotis, Angew. Chem. 2001, 113, 4507-4509; Angew. Chem. Int. Ed. 2001, 40, 4377-4379;
8. d) J.-A. Ma, Angew. Chem. 2003, 115, 4426-4435; Angew. Chem. Int. Ed. 2003, 42, 4290-4299;
9. d) J.-A. Ma, Angew. Chem. 2003, 115, 4426-4435; Angew. Chem. Int. Ed. 2003, 42, 4290-4299;
10. e) N. Sewald, Angew. Chem. 2003, 115, 5972-5973; Angew. Chem. Int. Ed. 2003, 42, 5794-5795.
11. e) N. Sewald, Angew. Chem. 2003, 115, 5972-5973; Angew. Chem. Int. Ed. 2003, 42, 5794-5795.
12. a) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475;
13. b) A. Fujii, E. Hagiwara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458;
14. c) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
15. For recent examples of the catalytic enantioselective Mannich reactions using preformed metal enolates: a) H. Fujieda, M. Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061;
16. b) H. Ishitani, M. Ueno, S, Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
17. c) S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334; Angew. Chem. Int. Ed. 2001,40, 2271-2274;
18. c) S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334; Angew. Chem. Int. Ed. 2001,40, 2271-2274;
19. d) D. Ferraris, B. Young, C. Cox, T. Dudding, W. J. Drury III, L. Ryzhkov, A. E. Taggi, T. Lectka, J. Am. Chem. Soc. 2002, 124, 67-77;
20. e) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641;
21. f) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964-12965;
22. g) S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507-2515;
23. h) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735;
24. i) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594; Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
25. i) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594; Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
26. j) S. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, Y. Yamashita, Proc. Natl. Acad. Sci. USA 2004, 101, 5476-5481.
27. S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis, Supplement 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2003, chap. 29.5, p. 143.
28. Recent examples of direct catalytic asymmetric Mannich reactions: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 8857-8867;
29. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085; Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
30. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085; Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
31. c) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
32. d) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
33. e) 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;
34. f) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301-4304;
35. g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808; Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
36. g) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808; Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
37. h) L. Bernardi, A. S. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583-2591;
38. i) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339;
39. j) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777-8785;
40. k) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
41. l) W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576-4578; Angew. Chem. Int. Ed. 2004, 43, 4476-4478;
42. l) W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576-4578; Angew. Chem. Int. Ed. 2004, 43, 4476-4478;
43. m) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558-560;
44. n) A. Córdova, Chem. Eur. J. 2004, 10, 1987-1997;
45. see also, o) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112.
46. a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240 -11241;
47. b) Y. Hamashima, K. Yagi, H. Takano, L. Támas, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530-14531;
48. c) Y. Hamashima, H. Takano, D. Hotta, M. Sodeoka, Org. Lett. 2003, 5, 3225-3228;
49. d) Y. Hamashima, M. Sodeoka, Chem. Rec. 2004, 4, 231-242.
50. M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367.
51. A report on the asymmetric synthesis of α-tetrasubstituted β-amino acids appeared during the preparation of this manuscript: N. S. Chowdari, J. T. Suri, C. F. Barbas III, Org. Lett. 2004, 6, 2507-2510.
52. A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
53. a) B. E. Love, P. S. Raje, T. C. Williams II, Synlett 1994, 493-494;
54. b) F. Chemla, V. Hebbe, J.-F. Normant, Synthesis 2000, 75-77.
55. S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782-2791.
56. See Supporting Information.
57. 1H NMR spectroscopy experiments will be discussed elsewhere. For details of characterization of the Pd enolate, see: Ref. [7a] and Supporting Information therein.
58. The reaction of 3 a with 5 a in the presence of 2 a was found to be less efficient than that in the case of 1 a under the same reaction conditions (0 °C, 5 hours) [1 a (2.5 mol%): see Table 2, entry 3; 2 a (5 mol% to Pd): 58%, d.r. = 89:11, 92% ee (major), 86% ee (minor)]. Similar diastereo- and enantioselectivities were obtained. However, the reaction rate was considerably slower in the case of 2 a, although the two-fold Pd complex was used. This clearly indicates that a proton plays a role in the acceleration of the reaction. Also, compare entries 7 and 8 in Table 1.
59. A recent example of the in situ generation of iminium ions by protonation of enamines: C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2002, 114, 2651-2654; Angew. Chem. Int. Ed. 2002, 41, 2535-2538.
60. A recent example of the in situ generation of iminium ions by protonation of enamines: C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2002, 114, 2651-2654; Angew. Chem. Int. Ed. 2002, 41, 2535-2538.
61. An open transition-state was proposed as an important candidate. See, D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059-1062; Angew. Chem. Int. Ed. Engl. 1996, 35, 981-984.
62. An open transition-state was proposed as an important candidate. See, D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059-1062; Angew. Chem. Int. Ed. Engl. 1996, 35, 981-984.
63. The involvement of the protonated imines raises another possibility. Seebach et al. have proposed an electrostatic interaction of a Ti enolate with an iminium cation in their anti-selective Mannich reaction. However, in our case, such a transition-state would cause severe steric repulsion between the protecting group of the imine and the Pd catalyst. See, a) D. Seebach, C. Betschart, M. Schiess, Helv. Chim. Acta 1984, 67, 1593-1597;
64. b) D. Seebach, M. Schiess, W. B. Schweizer, Chimia 1985, 39, 272-273.