Enantioselective synthesis of chromans with a quaternary stereogenic centre through catalytic asymmetric cascade reactions

ACS Catalysis

Volumn 1, Issue 3, 2011, Pages 221-226

  Hua, Qiu Lin ^a   Li, Chao ^a   Wang, Xu Fan ^a   Lu, Liang Qiu ^a   Chen, Jia Rong ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

cascade reaction; chromans; heterocycle; Michael addition; Organocatalysis

Indexed keywords

CASCADE REACTIONS; CHROMANS; HETEROCYCLES; MICHAEL ADDITIONS; ORGANOCATALYSIS;

ADDITION REACTIONS; CATALYSIS; ENANTIOSELECTIVITY; RATE CONSTANTS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

EID: 79952380987     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs100161k     Document Type: Article

References (94)

1. Schweizer, E. E.; Meeder-Nycz, O. Chromenes, Chromansses, and Chromones; Wiley-Interscience: New York, 1977.
2. Keay, B. A. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, p 395.
3. Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939-9953
4. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310
5. Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P.; Sylvain, C. J. Am. Chem. Soc. 2004, 126, 11966-11983
6. Shen, H. C. Tetrahedron 2009, 65, 3931-3952
7. De Cree, J.; Geukens, H.; Leempoels, J.; Verhaegen, H. Drug Dev. Res. 1986, 8, 109-117
8. Van de Water, A.; Janssens, W.; Van Nueten, J.; Xhonneux, R.; De Cree, J.; Verhaegen, H.; Reneman, R. S.; Janssen, P. A. J. J. Cardiovasc. Pharmacol. 1988, 11, 552-563
9. Kashiwada, Y.; Yamazaki, K.; Ikeshiro, Y.; Yamagishi, T.; Fujioka, T.; Mihashi, K.; Mizuki, K.; Cosention, L. M.; Fowke, K.; Morris-Natschke, S. L.; Lee, K.-H. Tetrahedron 2001, 57, 1559-1563
10. Kashman, Y.; Gustafson, K. R.; Fuller, R. W.; Cardellina, J. H.; Mcnahon, J. B.; Currens, M. J.; Buckhiet, R. W.; Hughes, S. H.; Cragg, G. M.; Boyd, M. R. J. Med. Chem. 1992, 35, 2735-2743
11. Taylor, P. B.; Culp, J. S.; Debouck, C.; Johnson, R. K.; Patil, A. D.; Woolf, D. J.; Brooks, I.; Hertzberg, R. P. J. Biol. Chem. 1994, 269, 6325-6331
12. Mente, N. R.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2008, 73, 7963-7970
13. Chapelat, J.; Buss, A.; Chougnet, A.; Woggon, W.-D. Org. Lett. 2008, 10, 5123-5126
14. Marcos, R.; Rodríguez-Escrich, C.; Herrerías, C. I.; Pericàs, M. I. J. Am. Chem. Soc. 2008, 130, 16838-16839
15. Khupse, R. S.; Erhardt, P. W. Org. Lett. 2008, 10, 5007-5010
16. Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2004, 43, 262-264
17. Tietze, L. F.; Stecker, F.; Zinngrebe, J.; Sommer, K. M. Chem.-Eur. J. 2006, 12, 8770-8776
18. Trost, B. M.; Toste, D. F. J. Am. Chem. Soc. 1998, 120, 9074-9075
19. Trost, B. M.; Shen, H. C.; Surviet, J. P. Angew. Chem., Int. Ed. 2003, 42, 3943-3947
20. Trost, B. M.; Shen, H. C.; Surivet, J.-P. J. Am. Chem. Soc. 2003, 125, 9276-9277
21. Fukamizu, K.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2008, 130, 10498-10499
22. Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123
23. Liu, K.; Chougnet, A.; Woggon, W.-D. Angew. Chem., Int. Ed. 2008, 47, 5827-5829
24. Chung, Y. K.; Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 2225-2227
25. Nicolaou, K. C.; Reingruber, R.; Sarlah, D.; Bräse, S. J. Am. Chem. Soc. 2009, 131, 2086-2087
26. Wu, X.; Zhou, J.; Snider, B. B. Angew. Chem., Int. Ed. 2009, 48, 1283-1286
27. Zu, L.-S.; Zhang, S.-L.; Xie, H.-X.; Wang, W. Org. Lett. 2009, 11, 1627-1630
28. Li, J.-L.; Zhou, S.-L.; Han, B.; Wu, L.; Chen, Y.-C. Chem. Commun. 2010, 2665-2667
29. Ramachary, D. B.; Sakthidevi, R. Chem.-Eur. J. 2009, 15, 4516-4522
30. Kotane, P.; Hong, B.-C.; Liao, J.-H. Tetrahedron Lett. 2009, 50, 704-707
31. Lu, H.-H.; Liu, H.; Wu, W.; Wang, X.-F.; Lu, L.-Q.; Xiao, W.-J. Chem.-Eur. J. 2009, 15, 2742-2746
32. Wang, X.-F.; Hua, Q.-L.; Cheng, Y.; An, X.-L.; Yang, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 8379-8383
33. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4 th ed.; Blackwell Science: Oxford, U.K., 2000.
34. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2 nd ed.; Pergamon: Oxford, UK, 2002.
35. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles, 2 nd ed.; Wiley-VCH: New York, 2003.
36. Purwanto, M. G. M.; Weisz, K. Curr. Org. Chem. 2003, 7, 427-446
37. Kale, R. R.; Prasad, V.; Mohapatra, P. P.; Tiwari, V. K. Monatsh. Chem. 2010, 141, 1159-1182
38. Njar, V. C.; Brodie, A. M. Drugs. 1999, 58, 233-255, and references cited therein
39. Mashraqui, S. H.; Kumar, S.; Mudaliar, C. D. Bull. Chem. Soc. Jpn. 2001, 74, 2133-2138
40. Kopanska, K.; Najda, A.; Zebrowska, J.; Chomicz, L.; Piekarczyk, J.; Myjak, P.; Bretner, M. Bioorg. Med. Chem. 2004, 12, 2617-2624
41. Zhou, T.; Lou, H. Carbohydr. Res. 2007, 342, 865-869
42. Gopi, H.; Umashankara, M.; Pirrone, V.; Lalonde, J.; Badani, N.; Tuzer, F.; Baxter, S.; Zentner, I.; Cocklin, S.; Jawanda, N.; Miller, S. R.; Schon, A.; Klein, J. C.; Freire, E.; Krebs, F. C.; Smith, A. B.; Sodroski, J.; Chaiken, I. J. Med. Chem. 2008, 51, 2638-2647
43. Bae, S.; Lakshman, M. K. J. Org. Chem. 2008, 73, 1311-1319
44. Yu, T.-Z.; Zhang, P.; Zhao, Y.-L.; Zhang, H.; Fan, D.-W.; Dong, W.-K.; Ding, L. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 2655-2663
45. Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany, 2007.
46. List, B. Asymmetric Organocatalysis; Springer: Heidelberg, Germany, 2010.
47. Pellissier, H. Recent Developments in Asymmetric Organocatalysis; The Royal Society of Chemistry: Cambridge, U.K., 2010.
48. Mukherjee, S.; Yang, J.-W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5469
49. MacMillan, D. W. C. Nature 2008, 455, 304-308
50. Adair, G.; Mukherjee, S.; List, B. Aldrichimica Acta 2008, 41, 31-39
51. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
52. Yu, X.-H.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037-2046
53. For an excellent review of cascade Michael/Michael reaction, see: Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010-1022
54. Zu, L.-S.; Li, H.; Xie, H.-X.; Wang, J.; Jiang, W.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732-3734
55. Li, H.; Zu, L.-S.; Xie, H.-S.; Wang, J.; Jiang, W.; Wang, W. Org. Lett. 2007, 9, 1833-1385
56. Sriramurthy, V.; Barcan, G. A.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12928-12929
57. Sun, X.; Sengupta, S.; Petersen, J. L.; Wang, H.; Lewis, J. P.; Shi, X.-D. Org. Lett. 2007, 9, 4495-4498
58. Tan, B.; Shi, Z.-G.; Chuan, P.-J.; Zhong, G.-F. Org. Lett. 2008, 10, 3425-3428
59. Tan, B.; Shi, Z.-G.; Chuan, P.-J.; Li, Y.; Zhong, G.-F. Org. Lett. 2008, 10, 2437-2440
60. Wang, J.; Xie, H.-X.; Li, H.; Zu, L.-S.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177-4179
61. Wu, L.-Y.; Bencivenni, G.; Mancinelli, M.; Mazzanti, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7196-7199
62. Zhang, X.-S.; Zhang, S.-L.; Wang, W. Angew. Chem., Int. Ed. 2010, 49, 1481-1484
63. To our knowledge, only one report about organocatalytic asymmetric aza-Michael/Michael addition reaction, see: Li, H.; Zu, L.-S.; Xie, H.-X.; Wang, J.; Wang, W. Chem. Commun. 2008, 5636-5638
64. Li, C.-F.; Liu, H.; Liao, J.; Cao, Y.-J.; Liu, X.-P.; Xiao, W.-J. Org. Lett. 2007, 9, 1847-1850
65. Lu, L.-Q.; Cao, Y.-J.; Liu, X.-P.; An, J.; Yao, C.-J.; Ming, Z.-H.; Xiao, W.-J. J. Am. Chem. Soc. 2008, 130, 6946-6948
66. Chen, J.-R.; Li, C.-F.; An, X.-L.; Zhang, J.-J.; Zhu, X.-Y.; Xiao, W.-J. Angew. Chem., Int. Ed. 2008, 47, 2489-2492
67. Lu, L.-Q.; Li, F.; An, J.; Zhang, J.-J.; An, X.-L.; Hua, Q.-L.; Xiao, W.-J. Angew. Chem., Int. Ed. 2009, 48, 9542-9545
68. Wang, X.-F.; Chen, J.-R.; Cao, Y.-J.; Cheng, H.-G.; Xiao, W.-J. Org. Lett. 2010, 12, 1140-1143
69. Lu, L.-Q.; Zhang, J.-J.; Li, F.; Cheng, Y.; An, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 4495-4498
70. For a recent review on organocatalytic asymmetric aza-Michael addition reaction, see: Enders, D.; Wang, C.; Liebich, J. X. Chem.-Eur. J. 2009, 15, 11058-11076
71. Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393-2397
72. Wang, J.; Li, H.; Zu, L.-S.; Wang, W. Org. Lett. 2006, 8, 1391-1394
73. Diner, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983-1987
74. Uria, U.; Vicario, J. L.; Badia, D.; Carrillo, L. Chem. Commun. 2007, 2509-2511
75. Wang, J.; Zu, L.-S.; Li, H.; Xie, H.-X.; Wang, W. Synthesis 2007, 2576-2580
76. Zhu, D.; Lu, M.; Chua, P.-J.; Tan, B.; Wang, F.; Yang, X.-H.; Zhong, G.-F. Org. Lett. 2008, 10, 4585-4588
77. Lu, M.; Zhu, D.; Lu, Y.-P.; Hou, Y.-X.; Tan, B.; Zhong, G.-F. Angew. Chem., Int. Ed. 2008, 47, 10187-10191
78. Luo, G.-S.; Zhang, S.-L.; Duan, W.-H.; Wang, W. Synthesis 2009, 1564-1572
79. Fang, L.; Lin, A.-J.; Jia, X.-F.; Meng, J.; Wang, Y.-N.; Zhu, C.-J. Lett. Org. Chem 2009, 6, 397-399
80. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673
81. Okino, T.; Hoashi, Y.; Furukawa, T.; Xue, X.-N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119-125
82. McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370
83. Ye, J.; Dixon, D. J.; Hynes, P. Chem. Commun. 2005, 4481-4483
84. Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048-6049
85. Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.-M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156-8157
86. Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Wu, X.-J. Chem. Commun. 2008, 1431
87. Wang, C.-J.; Dong, X.-Q.; Zhang, Z.-H.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606-8607
88. Dong, X.-Q.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2009, 11, 1265-1268
89. The configuration of 3d was determined by X-ray crystallographic analysis. CCDC 784759 (3d) 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.
90. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621-631
91. Inokuma, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2006, 128, 9413-9419
92. Ciganek, E. Synthesis 1995, 1311-1314
93. Denmark, S. E.; Senanayaket, C. B. W. J. Org. Chem. 1993, 58, 1853-1858
94. Martin, N. J. A.; Cheng, X.; List, B. J. Am. Chem. Soc. 2008, 130, 13862-13863