PdII-catalyzed asymmetric addition reactions of 1,3-dicarbonyl compounds: Mannich-type reactions with N-boc imines and three-component aminomethylation

Chemistry - An Asian Journal

Volumn 3, Issue 8-9, 2008, Pages 1443-1455

  Hamashima, Yoshitaka ^a   Sasamoto, Naoki ^a   Umebayashi, Natsuko ^a,b   Sodeoka, Mikiko ^a,b  

^a RIKEN   (Japan)

^b SAITAMA UNIVERSITY   (Japan)

Author keywords

1,3 dicarbonyl compounds; Aminomethylation; Mannich reactions; Palladium; Quaternary centers

Indexed keywords

EID: 54849421561     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800120     Document Type: Article

References (95)

1. a) E. F. Kleinman in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Flemming, C. H. Heathcock), Pergamon, Oxford, 1991, chapter. 4.1;
2. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122;
3. Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
4. For the synthesis of β-amino acids, see: Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley-VCH, New York, 1997.
5. For a review: a) S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis, Supplement 1 (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, pp. 143-150;
6. b) M. Liu, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035;
7. c) G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569;
8. d) M. Shibasaki, S. Matsunaga, J. Organomet. Chem. 2006, 691, 2089-2100.
9. Selected examples of the Mannich reaction using preformed metal enolates: a) H. Fujieda, M. Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061;
10. b) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
11. c) S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334;
12. Angew. Chem. Int. Ed. 2001, 40, 2271-2274;
13. 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;
14. e) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641;
15. f) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964-12965;
16. g) S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507-2515;
17. h) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734-3735;
18. i) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
19. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
20. j) S. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, Y. Yamashita, Proc. Natl. Acad. Sci. USA 2004, 101, 5476-5481;
21. k) N. S. Josephsohn, E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Org. Lett. 2005, 7, 2711-2713;
22. l) T. Hamada, K. Manabe, Kobayashi, Chem. Eur. J. 2006, 12, 1205-1215;
23. m) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764.
24. a) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475;
25. b) A. Fujii, E. Hagiwara, M. Sodeoka, J. Am. Chem. Soc. 1999, 121, 5450-5458;
26. c) A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
27. For a recent excellent review on the catalytic asymmetric direct Mannich reaction: a) A. CVrdova, Acc. Chem. Res. 2004, 37, 102-112;
28. b) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815.
29. Selected examples of direct metal-catalyzed asymmetric Mannich-type reactions; a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 8857-8867;
30. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085;
31. Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
32. c) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339;
33. d) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777-8785;
34. e) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439-4442;
35. Angew. Chem. Int. Ed. 2005, 44, 4365-4368;
36. f) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779;
37. g) H. Morimoto, G. Lu, N. Aoyama, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 9588-9589;
38. h) G. A. Cutting, N. E. Stainforth, M. P. John, G. Kociok-Köhn, M. C. Willis, J. Am. Chem. Soc. 2007, 129, 10632-10633.
39. Selected examples of direct organocatalytic Mannich-type reactions: a) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
40. b) A. CVrdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843;
41. c) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808;
42. Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
43. d) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
44. e) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. 2005, 117, 4147-4151;
45. Angew. Chem. Int. Ed. 2005, 44, 4079-4083;
46. f) T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408-16409;
47. g) I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760-1762;
48. h) T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 10054-10055;
49. i) J. Vesely, R. Rios, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2007, 48, 421-425;
50. j) H. Zhang, S. Mitsumori, N. Utsumi, M. Imai, N. Garcia-Delgado, M. Mifsud, K. Albertshofer, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2008, 130, 875-886;
51. k) J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List, Nature 2008, 452, 453-455.
52. Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem. 2005, 117, 1549-1553;
53. Angew. Chem. Int. Ed. 2005, 44, 1525-1529.
54. M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367.
55. Selected examples of catalytic asymmetric Mannich-type reactions of dicarbonyl compounds with acylimines: a) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11256-11257;
56. b) A. Ting, S. Lou, S. E. Schaus, Org. Lett. 2006, 8, 2003-2006;
57. c) J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048-6049;
58. d) A. L. Tillman, J. Ye, D. J. Dixon, Chem. Commun. 2006, 1191-1193;
59. e) O. Marianacci, G. Micheletti, L. Bernardi, F. Fini, M. Fochi, D. Pettersen, V. Sgarzani, A. Ricci, Chem. Eur. J. 2007, 13, 8338-8351;
60. f) Y. Yamaoka, H. Miyabe, Y. Yasui, Y. Takemoto, Synthesis 2007, 2571-2575;
61. g) J. Song, H.-W. Shih, L. Deng, Org. Lett. 2007, 9, 603-606;
62. h) S. Lou, P. Dai, S. E. Schaus, J. Org. Chem. 2007, 72, 9998-10008;
63. i) Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 2170-2171.
64. Recent examples of addition reactions to imines using other acidic pronucleophiles: With cyanoacetates: a) T. B. Poulsen, C. Alemparte, S. Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956-2959;
65. Angew. Chem. Int. Ed. 2005, 44, 2896-2899.
66. With β-ketophosphonates: b) A. Kjærsgaard, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 804-808.
67. With nitroalkanes: c) J. C. Anderson, G. P. Howell, R. M. Lawrence, C. S. Wilson, J. Org. Chem. 2005, 70, 5665-5670;
68. d) T. P. Yoon, E. N. Jacobsen, Angew. Chem. 2005, 117, 470-472;
69. Angew. Chem. Int. Ed. 2005, 44, 466-468, and references therein.
70. With glycine Schiff base: e) T. Shibuguchi, H. Mihara, A. Kuramochi, T. Ohshima, M. Shibasaki, Chem. Asian J. 2007, 2, 794-801.
71. With α,α-dicyanoolefin: f) T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc. 2007, 129, 1878-1879.
72. a) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240-11241;
73. b) Y. Hamashima, D. Hotta, N. Umebayashi, Y. Tsuchiya, T. Suzuki, M. Sodeoka, Adv. Synth. Catal. 2005, 347, 1576-1586.
74. A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
75. S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782-2791.
76. A space-filling model depicted in Figure 2 was generated based on MM3 calculation using CAChe 5.0.
77. a) M. Sodeoka, Y. Hamashima, Bull. Chem. Soc. Jpn. 2005, 78, 941-956;
78. b) M. Sodeoka, Y. Hamashima, Pure Appl. Chem. 2006, 78, 477-494.
79. a) D. Nama, P. S. Pregosin, A. Albinati, S. Rizzato, Organometallics 2007, 26, 2111-2121;
80. b) M. Kujime, S. Hikichi, M. Akita, Organometallics 2001, 20, 4049-4060;
81. For the formation of Ru enolate complexes of b-ketoesters: c) M. Althaus, C. Bonaccorsi, A. Mezzetti, F. Santoro, Organometallics 2006, 25, 3108-3110.
82. A protic acid is known to be a classical catalyst for Mannich reactions. In our case, the reaction of 3e with 4a proceeded in the presence of 5 mol% TfOH to afford a racemic product in 50% yield (20 h, room temperature).
83. a) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059-1062;
84. Angew. Chem. Int. Ed. Engl. 1996, 35, 981-984;
85. b) D. Enders, S. Oberbörsch, J. Adam, D. Ward, Synthesis 2002, 2737-2748.
86. a) I. Ibrahem, P. Dziedzic, A. Córdova, Synthesis 2006, 4060-4064;
87. b) Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 6804-6805;
88. c) B. Rodríguez, C. Bolm, J. Org. Chem. 2006, 71, 2888-2891;
89. d) B. Y. Chi, E. P. English, W. C. Pomerantz, W. S. Horne, L. A. Joyce, L. R. Alexander, W. S. Fleming, E. A. Hopkins, S. H. Gellman, J. Am. Chem. Soc. 2007, 129, 6050-6055.
90. I. Ibrahem, J. Casa, A. Córdova, Angew. Chem. 2004, 116, 6690-6693;
91. Angew. Chem. Int. Ed. 2004, 43, 6528-6531.
92. Y. Hamashima, H. Somei, Y. Shimura, T. Tamura, N. Sodeoka, Org. Lett. 2004, 6, 1861-1864.
93. 2: 81%, 55% ee (1.5 h); toluene: 99%, 68% ee (1.5 h); DMF: 75%, 49% ee (24 h); EtOH: 64%, 10% ee (24 h).
94. Lowering the reaction temperature improved the enantiomeric excess by <10% at the cost of the reaction rate. Thus, the reaction catalyzed by 1a at -20°C gave the product 15e in 66% yield with 64% ee after 15 h.
95. 2 were not available in this reaction, and the hydroxymethylated product alone was obtained.