Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

Angewandte Chemie - International Edition

Volumn 52, Issue 28, 2013, Pages 7310-7313

  Yin, Liang ^a   Takada, Hisashi ^a   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a,b  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

asymmetric catalysis; atom economy; cooperative catalysis; ketimines; synthetic methods

Indexed keywords

ASYMMETRIC CATALYSIS; ATOM ECONOMY; COOPERATIVE CATALYSIS; KETIMINES; SYNTHETIC METHODS;

CHEMISTRY;

CATALYSIS;

BUTENOLIDE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; IMINE; KETIMINE; KETONE; LEWIS ACID; NITRILE;

ARTICLE; ASYMMETRIC CATALYSIS; ATOM ECONOMY; CATALYSIS; CHEMISTRY; COOPERATIVE CATALYSIS; KETIMINES; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHETIC METHODS;

ASYMMETRIC CATALYSIS; ATOM ECONOMY; COOPERATIVE CATALYSIS; KETIMINES; SYNTHETIC METHODS;

4-BUTYROLACTONE; CATALYSIS; IMINES; KETONES; LEWIS ACIDS; NITRILES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84880175252     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303119     Document Type: Article

References (86)

1. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402
2. Angew. Chem. Int. Ed. 1998, 37, 388
3. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725
4. Angew. Chem. Int. Ed. 2001, 40, 4591
5. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363
6. Quaternary Stereocenters (Eds.:, J. Christoffer, A. Baro,), Wiley, Weinheim, 2005
7. B. M. Trost, C. Jiang, Synthesis 2006, 369
8. I. Marek, G. Sklute, Chem. Commun. 2007, 1683
9. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969.
10. B. M. Trost, Science 1991, 254, 1471.
11. X. Franck, B. Figadére, Tetrahedron Lett. 2002, 43, 1449
12. K. Das Sarma, J. Zhang, T. T. Curran, J. Org. Chem. 2007, 72, 3311.
13. A. Yamaguchi, S. Matsunaga, M. Shibasaki, Org. Lett. 2008, 10, 2319
14. L. Zhou, L. Lin, J. Ji, M. Xie, X. Liu, X. Feng, Org. Lett. 2011, 13, 3056
15. Y.-L. Guo, J.-F. Bai, L. Peng, L.-L. Wang, L.-N. Jia, X.-Y. Luo, F. Tian, X.-Y. Xu, L.-X. Wang, J. Org. Chem. 2012, 77, 8338.
16. H. Ube, N. Shimada, M. Terada, Angew. Chem. 2010, 122, 1902
17. Angew. Chem. Int. Ed. 2010, 49, 1858
18. Y. Yang, K. Zheng, J. Zhao, J. Shi, L. Lin, X. Liu, X. Feng, J. Org. Chem. 2010, 75, 5382
19. S. V. Pansare, E. K. Paul, Chem. Commun. 2011, 47, 1027
20. S. V. Pansare, E. K. Paul, Org. Biomol. Chem. 2012, 10, 2119.
21. B. M. Trost, J. Hitce, J. Am. Chem. Soc. 2009, 131, 4572
22. Y. Zhang, C. Yu, Y. Ji, W. Wang, Chem. Asian J. 2010, 5, 1303
23. J. Wang, C. Qi, Z. Ge, T. Cheng, R. Li, Chem. Commun. 2010, 46, 2124
24. M. Terada, K. Ando, Org. Lett. 2011, 13, 2026.
25. For a direct catalytic asymmetric Mannich reaction and a Michael reaction of α,β-unsaturated γ-butyrolactams:, N. E. Shepherd, H. Tanabe, Y. Xu, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 3666.
26. E.-I. Negishi, M. Kotora, Tetrahedron 1997, 53, 6707
27. G. Casiraghi, F. Zanardi, L. Battistini, G. Rassu, G. Appendino, Chemtracts 1998, 11, 803
28. F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504
29. R. Bruckner, Curr. Org. Chem. 2001, 5, 679
30. T. Montagnon, M. Tofi, G. Vassilikogiannakis, Acc. Chem. Res. 2008, 41, 1001
31. T. M. Ugurchieva, V. V. Veselovsky, Russ. Chem. Rev. 2009, 78, 337.
32. 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
33. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541
34. S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626.
35. M. M. B. Marques, Angew. Chem. 2006, 118, 356
36. Angew. Chem. Int. Ed. 2006, 45, 348
37. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797
38. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29
39. R. Gõmez Arrayás, J. C. Carretero, Chem. Soc. Rev. 2009, 38, 1940.
40. S. K. Bur, S. F. Martin, Tetrahedron 2001, 57, 3221
41. S. F. Martin, Acc. Chem. Res. 2002, 35, 895
42. G. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076.
43. L. C. Wieland, E. M. Vieira, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 570. After submission of this manuscript, a catalytic asymmetric vinylogous Mannnich-type reaction using 2-siloxyfuran and diphenylphosphinoyl ketimines was reported
44. M. Hayashi, M. Sano, Y. Funahashi, S. Nakamura, Angew. Chem. 2013, 125, 5667
45. Angew. Chem. Int. Ed. 2013, 52, 5557.
46. S. Saaby, K. Nakama, M. A. Lie, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 6145
47. W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576
48. Angew. Chem. Int. Ed. 2004, 43, 4476
49. B. Jiang, J. J. Dong, Y. G. Si, X. L. Zhao, Z. G. Huang, M. Xu, Adv. Synth. Catal. 2008, 350, 1360
50. N. Hara, S. Nakamura, M. Sano, R. Tamura, Y. Funahashi, N. Shibata, Chem. Eur. J. 2012, 18, 9276
51. W. Yan, D. Wang, J. Feng, P. Li, D. Zhao, R. Wang, Org. Lett. 2012, 14, 2512
52. T. Kano, S. Song, Y. Kubota, K. Maruoka, Angew. Chem. 2012, 124, 1217
53. 3 group, see
54. V. A. Sukach, N. M. Golovach, V. V. Pirozhenko, E. B. Rusanov, M. V. Vovk, Tetrahedron: Asymmetry 2008, 19, 761
55. N. Hara, R. Tamura, Y. Funahashi, S. Nakamura, Org. Lett. 2011, 13, 1662.
56. G. Lu, T. Yoshino, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2011, 123, 4474
57. Angew. Chem. Int. Ed. 2011, 50, 4382. For catalytic asymmetric Mannich reactions of nonactivated ketimines using organometallic reagents
58. Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 500
59. Y. Du, L.-W. Xu, Y. Shimiza, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 16146. For catalytic asymmetric self-coupling of ketone-derived enamides
60. C. Baudequin, A. Zamfir, S. B. Tsogoeva, Chem. Commun. 2008, 4637. See also Ref. [13b].
61. X. Xu, C. Wang, Z. Zhou, Z. Zeng, X. Ma, G. Zhao, C. Tang, Lett. Org. Chem. 2006, 3, 640
62. X. Xu, C. Wang, Z. Zhou, Z. Zeng, X. Ma, G. Zhao, C. Tang, Heteroat. Chem. 2008, 19, 238. Application of N-(thiophosphinoyl)imines as electrophiles
63. X. Ma, C. Wang, X. Xu, G. Zhao, Z. Zhou, C. Tang, Lett. Org. Chem. 2007, 4, 51
64. X. Ma, X. Xu, C. Wang, G. Zhao, Z. Zhou, C. Tang, J. Organomet. Chem. 2007, 692, 3685
65. X. Xu, C. Wang, Z. Zhou, X. Tang, Z. He, C. Tang, Eur. J. Org. Chem. 2007, 4487
66. A. Lu, X. Xu, P. Gao, Z. Zhou, H. Song, C. Tang, Tetrahedron: Asymmetry 2008, 19, 1886
67. B. Zhang, Z. He, S. Xu, G. Wu, Z. He, Tetrahedron 2008, 64, 9471
68. K. Hu, C. Wang, X. Ma, Y. Wang, Z. Zhou, C. Tang, Tetrahedron: Asymmetry 2009, 20, 2178.
69. L. Yin, Y. Otsuka, H. Takada, S. Mouri, R. Yazaki, N. Kumagai, M. Shibasaki, Org. Lett. 2013, 15, 698.
70. M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187
71. N. Kumagai, M. Shibasaki, Angew. Chem. 2011, 123, 4856
72. Angew. Chem. Int. Ed. 2011, 50, 4760. Lewis acid/Lewis base
73. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491
74. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655. Lewis acid/Brønsted acid and Lewis acid/Lewis acid
75. H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958
76. Angew. Chem. Int. Ed. 2005, 44, 1924
77. H. Yamamoto, K. Futatsugi, in Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008.
78. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 5522
79. M. Iwata, R. Yazaki, I.-H. Chen, D. Sureshkumar, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2011, 133, 5554.
80. T. Ireland, G. Grossheimann, C. Wieser-Jeunesse, P. Knochel, Angew. Chem. 1999, 111, 3397
81. Angew. Chem. Int. Ed. 1999, 38, 3212
82. T. Ireland, K. Tappe, G. Grossheimann, P. Knochel, Chem. Eur. J. 2002, 8, 843
83. S. Fukuzawa, M. Yamamoto, M. Hosaka, S. Kikuchi, Eur. J. Org. Chem. 2007, 5540.
84. The absolute and relative configuration of 3 a was determined by X-ray crystallographic analysis. CCDC 932229 (3 a) contains 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. A summary of the crystallographic analysis of 3 a is provided in the Supporting Information.
85. R. Paul, P. Buisson, N. Joseph, Ind. Eng. Chem. 1952, 44, 1006
86. C. W. Jefford, D. Jaggi, G. Bernardinelli, J. Boukouvalas, Tetrahedron Lett. 1987, 28, 4041.