Catalytic Asymmetric Diels-Alder Reaction of Quinone Imine Ketals: A Site-Divergent Approach

Angewandte Chemie - International Edition

Volumn 54, Issue 15, 2015, Pages 4617-4621

  Hashimoto, Takuya ^a   Nakatsu, Hiroki ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; Br nsted acids; carboxylic acids; Diels Alder reactions; quinones

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; NITROGEN COMPOUNDS;

ASYMMETRIC CATALYSIS; DICARBOXYLIC ACID; DIELS-ALDER REACTION; DIVERGENT APPROACH; QUINONE-IMINES; QUINONES; REACTION SITES;

CHEMICAL REACTIONS;

EID: 85027958406     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410957     Document Type: Article

References (59)

1. C. C. Nawrat, C. J. Moody, Angew. Chem. Int. Ed. 2014, 53, 2056
2. Angew. Chem. 2014, 126, 2086.
3. K. Mikami, M. Terada, Y. Motoyama, T. Nakai, Tetrahedron: Asymmetry 1991, 2, 643
4. K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812
5. T. A. Engler, M. A. Letavic, F. Takusagawa, Tetrahedron Lett. 1992, 33, 6731
6. T. A. Engler, M. A. Letavic, K. O. Lynch, F. Takusagawa, J. Org. Chem. 1994, 59, 1179
7. J. D. White, Y. Choi, Org. Lett. 2000, 2, 2373
8. D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 6388
9. D. H. Ryu, G. Zhou, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 4800
10. D. A. Evans, J. Wu, J. Am. Chem. Soc. 2003, 125, 10162
11. E. R. Jarvo, B. M. Lawrence, E. N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 6043
12. Angew. Chem. 2005, 117, 6197
13. K. Futatsugi, H. Yamamoto, Angew. Chem. Int. Ed. 2005, 44, 1484
14. Angew. Chem. 2005, 117, 1508
15. J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9536.
16. Z.-Y. Han, D.-F. Chen, Y.-Y. Wang, R. Guo, P.-S. Wang, C. Wang, L.-Z. Gong, J. Am. Chem. Soc. 2012, 134, 6532
17. L. Albrecht, C. V. Gómez, C. B. Jacobsen, K. A. Jørgensen, Org. Lett. 2013, 15, 3010
18. T. K. Johansen, C. V. Gomez, J. R. Bak, R. L. Davis, K. A. Jørgensen, Chem. Eur. J. 2013, 19, 16518
19. F. Portalier, F. Bourdreux, J. Marrot, X. Moreau, V. Coeffard, C. Greck, Org. Lett. 2013, 15, 5642
20. C. Martín-Santos, C. Jarava-Barrera, S. dela Pozo, A. Parra, S. Díaz-Tendero, R. Mas-Ballesté, S. Cabrera, J. Alemán, Angew. Chem. Int. Ed. 2014, 53, 8184
21. Angew. Chem. 2014, 126, 8323.
22. For the use of in situ generated methylquinone, see Ref. [3d].
23. M. Breuning, E. J. Corey, Org. Lett. 2001, 3, 1559.
24. M. A. Kerr, Synlett 1995, 1165
25. S. C. Banfield, D. B. England, M. A. Kerr, Org. Lett. 2001, 3, 3325
26. S. C. Banfield, M. A. Kerr, Can. J. Chem. 2004, 82, 131.
27. T. Hashimoto, H. Nakatsu, Y. Takiguchi, K. Maruoka, J. Am. Chem. Soc. 2013, 135, 16010
28. L. Liao, C. Shu, M. Zhang, Y. Liao, X. Hu, Y. Zhang, Z. Wu, W. Yuan, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 10471
29. Angew. Chem. 2014, 126, 10639
30. Y.-C. Zhang, F. Jiang, S.-L. Wang, F. Shi, S.-J. Tu, J. Org. Chem. 2014, 79, 6143
31. Y.-C. Zhang, J.-J. Zhao, F. Jiang, S.-B. Sun, F. Shi, Angew. Chem. Int. Ed. 2014, 53, 13912
32. Angew. Chem. 2014, 126, 14132.
33. T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 10054
34. T. Hashimoto, K. Maruoka, Synthesis 2008, 3703
35. T. Hashimoto, H. Kimura, H. Nakatsu, K. Maruoka, J. Org. Chem. 2011, 76, 6030.
36. J. Mahatthananchai, J. W. Bode, A. M. Dumas, Angew. Chem. Int. Ed. 2012, 51, 10954
37. Angew. Che. 2012, 124, 11114.
38. P. A. Lichtor, S. J. Miller, Nat. Chem. 2012, 4, 990
39. A. D. Worthy, X. Sun, K. L. Tan, J. Am. Chem. Soc. 2012, 134, 7321
40. K. Akagawa, J. Sen, K. Kudo, Angew. Chem. Int. Ed. 2013, 52, 11585
41. Angew. Chem. 2013, 125, 11799.
42. The reaction with cyclopentadiene or 1-methoxybutadiene gave cycloadducts in modest yield and low enantioselectivity. Subsequent aromatization of the cycloadducts was observed.
43. L. E. Overman, G. F. Taylor, C. B. Petty, P. J. Jessup, J. Org. Chem. 1978, 43, 2164
44. L. E. Overman, P. J. Jessup, J. Am. Chem. Soc. 1978, 100, 5179.
45. M. Ronn, Z. Zhu, P. C. Hogan, W.-Y. Zhang, J. Niu, C. E. Katz, N. Dunwoody, O. Gilicky, Y. Deng, D. K. Hunt, M. He, C.-L. Chen, C. Sun, R. B. Clark, X.-Y. Xiao, Org. Process Res. Dev. 2013, 17, 838.
46. V. E. Gouverneur, K. N. Houk, B. de Pascual-Teresa, B. Beno, K. D. Janda, R. A. Lerner, Science 1993, 262, 204
47. P. Wipf, X. Wang, Tetrahedron Lett. 2000, 41, 8747
48. J. B. Siegel, A. Zanghellini, H. M. Lovick, G. Kiss, A. R. Lambert, J. L. St. Clair, J. L. Gallaher, D. Hilvert, M. H. Gelb, B. L. Stoddard, K. N. Houk, F. E. Michael, D. Baker, Science 2010, 329, 309
49. N. Momiyama, T. Konno, Y. Furiya, T. Iwamoto, M. Terada, J. Am. Chem. Soc. 2011, 133, 19294.
50. Y. Huang, T. Iwama, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 5950
51. Y. Huang, T. Iwama, V. H. Rawal, Org. Lett. 2002, 4, 1163.
52. The azide-free synthesis of diene carbamates from the corresponding aldehydes was developed (see the Supporting Information).
53. T. Hashimoto, T. Takagaki, H. Kimura, K. Maruoka, Chem. Asian J. 2011, 6, 1936
54. T. Hashimoto, H. Kimura, Y. Kawamata, K. Maruoka, Nat. Chem. 2011, 3, 642
55. T. Hashimoto, M. Omote, K. Maruoka, Angew. Chem. Int. Ed. 2011, 50, 8952
56. Angew. Chem. 2011, 123, 9114
57. T. Hashimoto, Y. Takiguchi, K. Maruoka, J. Am. Chem. Soc. 2013, 135, 11473.
58. Use of benzoic acid as a simple carboxylic acid led to site selectivity of 9:1 in favor of the isomer A.
59. We assumed that the carboxylic acid moiety of the catalyst simultaneously undergoes hydrogen bonding with both substrates in the transition state, according to previous studies (Refs. [7] and [14]).