N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β-Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives

Angewandte Chemie - International Edition

Volumn 53, Issue 43, 2014, Pages 11611-11615

  Chen, Xiang Yu ^a   Gao, Zhong Hua ^a   Song, Chun Yu ^b   Zhang, Chun Lin ^a   Wang, Zhi Xiang ^b   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

cyclization; heterocycles; N heterocyclic carbenes; organocatalysis; synthetic methods

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; IN SITU PROCESSING; KETONES; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLOCONDENSATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLES; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS; SYNTHETIC METHODS; UNSATURATED CARBOXYLIC ACIDS;

ORGANIC COMPOUNDS;

EID: 84941029473     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407469     Document Type: Article

References (109)

1. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606;
2. J. L. Moore, T. Rovis, Top. Curr. Chem. 2010, 291, 77;
3. X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511;
4. A. Grossmann, D. Enders, Angew. Chem. Int. Ed. 2012, 51, 314;
5. Angew. Chem. 2012, 124, 320;
6. J. Izquierdo, G. E. Hutson, D. T. Cohen, K. A. Scheidt, Angew. Chem. Int. Ed. 2012, 51, 11686;
7. Angew. Chem. 2012, 124, 11854;
8. H. U. Vora, P. Wheeler, T. Rovis, Adv. Synth. Catal. 2012, 354, 1617;
9. X.-Y. Chen, S. Ye, Synlett 2013, 1614;
10. S. J. Ryan, L. Candish, D. W. Lupton, Chem. Soc. Rev. 2013, 42, 4906;
11. J. W. Bode, Nat. Chem. 2013, 5, 813;
12. J. Mahatthananchai, J. W. Bode, Acc. Chem. Res. 2014, 47, 696.
13. T. Ugai, S. Tanaka, S. Dokawa, J. Pharm. Soc. Jpn. 1943, 63, 296;
14. R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719;
15. H. Stetter, M. Schrecke, Angew. Chem. Int. Ed. Engl. 1973, 12, 81;
16. Angew. Chem. 1973, 85, 89;
17. D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J. P. Melder, K. Ebel, S. Brode, Angew. Chem. Int. Ed. Engl. 1995, 34, 1021;
18. Angew. Chem. 1995, 107, 1119;
19. C. Burstein, F. Glorius, Angew. Chem. Int. Ed. 2004, 43, 6205;
20. Angew. Chem. 2004, 116, 6331;
21. N. T. Reynolds, J. R. deAlaniz, T. Rovis, J. Am. Chem. Soc. 2004, 126, 9518;
22. S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370;
23. G.-Q. Li, Y. Li, L.-X. Dai, S.-L. You, Adv. Synth. Catal. 2008, 350, 1258;
24. X. Huang, S. Ye, Chin. Sci. Bull. 2010, 55, 1753;
25. Y. Cheng, J.-H. Peng, Y.-J. Li, X.-Y. Shi, M.-S. Tang, T.-Y. Tan, J. Org. Chem. 2011, 76, 1844.
26. Y.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye, Org. Lett. 2008, 10, 277;
27. N. Duguet, C. D. Campbell, A. M. Z. Slawin, A. D. Smith, Org. Biomol. Chem. 2008, 6, 1108;
28. X.-L. Huang, L. He, P.-L. Shao, S. Ye, Angew. Chem. Int. Ed. 2009, 48, 192;
29. Angew. Chem. 2009, 121, 198;
30. P.-L. Shao, X.-Y. Chen, S. Ye, Angew. Chem. Int. Ed. 2010, 49, 8412;
31. Angew. Chem. 2010, 122, 8590.
32. L. Hao, Y. Du, H. Lv, X. Chen, H. Jiang, Y. Shao, Y. R. Chi, Org. Lett. 2012, 14, 2154;
33. S. Chen, L. Hao, Y. Zhang, B. Tiwari, Y. R. Chi, Org. Lett. 2013, 15, 5822;
34. Z. Fu, J. Xu, T. Zhu, W. W. Y. Leong, Y. R. Chi, Nat. Chem. 2013, 5, 835;
35. L. Hao, S. Chen, J. Xu, B. Tiwari, Z. Fu, T. Li, J. Lim, Y. R. Chi, Org. Lett. 2013, 15, 4956;
36. J. Xu, Z. Jin, Y. R. Chi, Org. Lett. 2013, 15, 5028;
37. P. Chauhan, D. Enders, Angew. Chem. Int. Ed. 2014, 53, 1485;
38. Angew. Chem. 2014, 126, 1509.
39. C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 1472;
40. L. He, T.-Y. Jian, S. Ye, J. Org. Chem. 2007, 72, 7466;
41. S.-I. Matsuoka, Y. Ota, A. Washio, A. Katada, K. Ichioka, K. Takagi, M. Suzuki, Org. Lett. 2011, 13, 3722;
42. A. T. Biju, M. Padmanaban, N. E. Wurz, F. Glorius, Angew. Chem. Int. Ed. 2011, 50, 8412;
43. Angew. Chem. 2011, 123, 8562;
44. R. L. Atienza, H. S. Roth, K. A. Scheidt, Chem. Sci. 2011, 2, 1772;
45. X.-Y. Chen, L.-H. Sun, S. Ye, Chem. Eur. J. 2013, 19, 4441.
46. S. De Sarkar, A. Studer, Angew. Chem. Int. Ed. 2010, 49, 9266;
47. Angew. Chem. 2010, 122, 9452;
48. Z.-Q. Rong, M.-Q. Jia, S.-L. You, Org. Lett. 2011, 13, 4080;
49. B. Wanner, J. Mahatthananchai, J. W. Bode, Org. Lett. 2011, 13, 5378;
50. A. G. Kravina, J. Mahatthananchai, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 9433;
51. Angew. Chem. 2012, 124, 9568;
52. B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett. 2007, 9, 371;
53. J. Guin, S. D. Sarkar, S. Grimme, A. Studer, Angew. Chem. Int. Ed. 2008, 47, 8727;
54. Angew. Chem. 2008, 120, 8855;
55. S. D. Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190;
56. B. Maji, S. Vedachalan, X. Ge, S. Cai, X.-W. Liu, J. Org. Chem. 2011, 76, 3016.
57. J. Kaeobamrung, J. Mahatthananchai, P. Zheng, J. W. Bode, J. Am. Chem. Soc. 2010, 132, 8810;
58. J. Mahatthananchai, P. Zheng, J. W. Bode, Angew. Chem. Int. Ed. 2011, 50, 1673;
59. Angew. Chem. 2011, 123, 1711;
60. J. Mahatthananchai, J. Kaeobamrung, J. W. Bode, ACS Catal. 2012, 2, 494;
61. Z.-Q. Zhu, X.-L. Zheng, N.-F. Jiang, X. Wan, J.-C. Xiao, Chem. Commun. 2011, 47, 8670;
62. Z.-Q. Zhu, J.-C. Xiao, Adv. Synth. Catal. 2010, 352, 2455.
63. F.-G. Sun, L.-H. Sun, S. Ye, Adv. Synth. Catal. 2011, 353, 3134;
64. S. R. Yetra, A. Bhunia, A. Patra, M. V. Mane, K. Vanka, A. T. Biju, Adv. Synth. Catal. 2013, 355, 1089;
65. S. R. Yetra, T. Kaicharla, S. S. Kunte, R. G. Gonnade, A. T. Biju, Org. Lett. 2013, 15, 5202;
66. C. Yao, D. Wang, J. Lu, T. Li, W. Jiao, C. Yu, Chem. Eur. J. 2012, 18, 1914.
67. L. Candish, C. M. Forsyth, D. W. Lupton, Angew. Chem. Int. Ed. 2013, 52, 9149;
68. Angew. Chem. 2013, 125, 9319;
69. S. J. Ryan, L. Candish, D. W. Lupton, J. Am. Chem. Soc. 2011, 133, 4694;
70. L. Candish, D. W. Lupton, J. Am. Chem. Soc. 2013, 135, 58.
71. S. J. Ryan, L. Candish, D. W. Lupton, J. Am. Chem. Soc. 2009, 131, 14176;
72. J. Cheng, Z. Huang, Y. R. Chi, Angew. Chem. Int. Ed. 2013, 52, 8592;
73. Angew. Chem. 2013, 125, 8754.
74. G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945;
75. S. H. Oh, G. S. Cortez, D. Romo, J. Org. Chem. 2005, 70, 2835;
76. H. Henry-Riyad, C. Lee, V. C. Purohit, D. Romo, Org. Lett. 2006, 8, 4363;
77. G. Ma, H. Nguyen, D. Romo, Org. Lett. 2007, 9, 2143;
78. V. C. Purohit, A. S. Matla, D. Romo, J. Am. Chem. Soc. 2008, 130, 10478;
79. C. A. Leverett, V. C. Purohit, D. Romo, Angew. Chem. Int. Ed. 2010, 49, 9479;
80. Angew. Chem. 2010, 122, 9669;
81. H. Nguyen, G. Ma, T. Gladysheva, T. Fremgen, D. Romo, J. Org. Chem. 2011, 76, 2.
82. D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin, A. D. Smith, J. Am. Chem. Soc. 2011, 133, 2714;
83. L. C. Morrill, T. Lebl, A. M. Z. Slawin, A. D. Smith, Chem. Sci. 2012, 3, 2088;
84. C. Simal, T. Lebl, A. M. Z. Slawin, A. D. Smith, Angew. Chem. Int. Ed. 2012, 51, 3653;
85. Angew. Chem. 2012, 124, 3713;
86. L. C. Morrill, J. Douglas, T. Lebl, A. M. Z. Slawin, D. J. Fox, A. D. Smith, Chem. Sci. 2013, 4, 4146;
87. L. C. Morrill, S. M. Smith, A. M. Z. Slawin, A. D. Smith, J. Org. Chem. 2014, 79, 1640;
88. S. R. Smith, J. Douglas, H. Prevet, P. Shapland, A. M. Z. Slawin, A. D. Smith, J. Org. Chem. 2014, 79, 1626; for their non-enantioselective reactions using this strategy, see:
89. D. G. Stark, L. C. Morrill, P.-P. Yeh, A. M. Z. Slawin, T. J. C. O'Riordan, A. D. Smith, Angew. Chem. Int. Ed. 2013, 52, 11642;
90. Angew. Chem. 2013, 125, 11856;
91. P.-P. Yeh, D. S. B. Daniels, D. B. Cordes, A. M. Z. Slawin, A. D. Smith, Org. Lett. 2014, 16, 964.
92. E. R. T. Robinson, C. Fallan, C. Simal, A. M. Z. Slawin, A. D. Smith, Chem. Sci. 2013, 4, 2193.
93. S. Vellalath, K. N. Van, D. Romo, Angew. Chem. Int. Ed. 2013, 52, 13688;
94. Angew. Chem. 2013, 125, 13933.
95. S. Goudedranche, X. Bugaut, T. Constantieux, D. Bonne, J. Rodriguez, Chem. Eur. J. 2014, 20, 410.
96. T. Mori, K. Takahashi, M. Kashiwabara, D. Uemura, Tetrahedron Lett. 1985, 26, 1073;
97. M. Anada, O. Mita, H. Watanabe, S. Kitagaki, S. Hashimoto, Synlett 1999, 1775;
98. M. A. Rogawski, Br. J. Pharmacol. 2008, 154, 1555;
99. T. A. Gulder, B. S. Moore, Angew. Chem. Int. Ed. 2010, 49, 9346;
100. Angew. Chem. 2010, 122, 9534.
101. M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204;
102. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766;
103. X. Zhao, D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2011, 133, 12466.
104. M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418.
105. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796;
106. J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798;
107. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992.
108. CCDC 997053 (4 k) and 997054 (6 c) contain 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.
109. During the resubmission of the manuscript, Scheidt et al. reported an NHC-catalyzed enantioselective annulation for dihydroquinolones by in situ generation of azolium enolates from carboxylic acids; see:, A. Lee, A. Younai, C. K. Price, J. Izquierdo, R. K. Mishra, K. A. Scheidt, J. Am. Chem. Soc. 2014, 136, 10589.