Catalytic asymmetric synthesis of enantioenriched heterocycles bearing a C-CF3 stereogenic center

Chemistry - A European Journal

Volumn 21, Issue 24, 2015, Pages 8664-8684

  Huang, Yi Yong ^a   Yang, Xing ^a   Chen, Zhuo ^a   Verpoort, Francis ^a   Shibata, Norio ^b  

^a WUHAN UNIVERSITY OF TECHNOLOGY   (China)

^b NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

asymmetric synthesis; heterocycles; organocatalysts; organometallic catalysis; trifluoromethylation

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; CHELATION; COST EFFECTIVENESS; ENANTIOSELECTIVITY; ORGANOMETALLICS;

ASYMMETRIC SYNTHESIS; HETEROCYCLES; ORGANOCATALYSTS; ORGANOMETALLIC CATALYSIS; TRIFLUOROMETHYLATION;

SELECTIVE CATALYTIC REDUCTION;

HETEROCYCLIC CARBOXYLIC ACID;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACIDS, HETEROCYCLIC; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84930202739     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500361     Document Type: Article

References (217)

1. S. Eguchi, Bioactive Heterocycles I, Springer, Heidelberg, 2006.
2. A. V. Gulevich, A. S. Dudnik, N. Chernyak, V. Gevorgyan, Chem. Rev. 2013, 113, 3084-3213
3. X.-F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, 1-35
4. C.-Y. Huang, A. G. Doyle, Chem. Rev. 2014, 114, 8153-8198.
5. T. Fujita, J. Iwasa, C. Hansch, J. Am. Chem. Soc. 1964, 86, 5175-5180
6. A. Leo, C. Hansch, D. Elkins, Chem. Rev. 1971, 71, 525-616
7. A. R. Katritzky, V. S. Lobanov, M. Karelson, Chem. Soc. Rev. 1995, 24, 279-287.
8. R. M. Wilson, S. J. Danishefsky, Angew. Chem. Int. Ed. 2010, 49, 6032-6056
9. Angew. Chem. 2010, 122, 6168-6193.
10. Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, West Sussex, 2008, pp. 1-624
11. Asymmetric Fluoroorganic Chemistry, ACS Symposium Series, Vol. 746 (Ed.:, P. V. Ramachandran,), American Chemical Society, Washington, DC, 2000
12. M. Abid, B. Torok, Adv. Synth. Catal. 2005, 347, 1797-1803
13. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455-529
14. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52, 8214-8264
15. Angew. Chem. 2013, 125, 8372-8423
16. X.-Y. Yang, T. Wu, R. J. Phipps, F. D. Toste, Chem. Rev. 2015, 115, 826-870
17. Fluorinated Heterocyclic Compounds: Synthesis Chemistry, and Applications (Ed.:, V. A. Petrov,), DuPont Central Research and Development, Wilmington, 2009
18. A. A. Gakh, K. L. Kirk, Fluorinated Heterocycles, ACS Symposium Series, Vol. 1003, American Chemical Society, Washington, DC, 2009
19. "Fluorine-Containing Heterocycles, Part I, Synthesis by Intramolecular Cyclization": G. F. Georgii, Advances in Heterocyclic Chemistry, Vol. 86 (Ed.:, A. R. Katritzky,), Elsevier, Amsterdam, 2004, pp. 129-224
20. H. Kawai, N. Shibata, Chem. Rec. 2014, 14, 1024-1040.
21. Y.-L. Liu, J.-L. Chen, G.-H. Wang, P. Sun, H.-Y. Huang, F.-L. Qing, Tetrahedron Lett. 2013, 54, 5541-5543
22. T. Mita, Y. Kudo, T. Mizukoshi, H. Hotta, K. Maeda, S. Takii, WO2004018410, 2004
23. G. Chaume, N. Lensen, C. Caupène, T. Brigaud, Eur. J. Org. Chem. 2009, 5717-5724
24. Y. Kohno, K. Awano, M. Miyashita, T. Ishizaki, K. Kuriyama, Y. Sakoe, S. Kudoh, K. Saito, E. Kojima, Bioorg. Med. Chem. Lett. 1997, 7, 1519-1524
25. S. Caron, N. M. Do, J. E. Sieser, P. Arpin, E. Vazquez, Org. Process Res. Dev. 2007, 11, 1015-1024
26. D. L. Romero, Annu. Rep. Med. Chem. 1994, 29, 123-132
27. J. W. Corbett, S. S. Ko, J. D. Rodgers, L. A. Gearhart, N. A. Magnus, L. T. Bacheler, S. Diamond, S. Jeffrey, R. M. Klabe, B. C. Cordova, S. Garber, K. Logue, G. L. Trainor, P. S. Anderson, S. K. Erickson-Viitanen, J. Med. Chem. 2000, 43, 2019-2030
28. G. Magueur, B. Crousse, S. Charneau, P. Grellier, J.-P. Bégué, D. Bonnet-Delpon, J. Med. Chem. 2004, 47, 2694-2699
29. B.-L. Wang, Z.-X. Jiang, Z.-W. You, F.-L. Qing, Tetrahedron 2007, 63, 12671-12680.
30. J. P. Bégué, D. Bonnet-Delpon, B. Crousse, J. Legros, Chem. Soc. Rev. 2005, 34, 562-572
31. X. Yang, Z. Chen, Y. Cai, Y.-Y. Huang, N. Shibata, Green Chem. 2014, 16, 4530-4534.
32. C. M. R. Volla, L. Atodiresei, M. Rueping, Chem. Rev. 2014, 114, 2390-2431
33. Privileged Chiral Ligands and Catalysts (Ed.:, Q.-L. Zhou,), Wiley-VCH, Weinheim, 2011
34. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis (I-III), Springer, Berlin, 1999
35. G.-Q. Lin, X.-W. Sun, Y.-Q. Chen, Y.-M. Li, X.-Z. Chen, Chiral Synthesis-Principles and Application of Asymmetric Reaction, Science, Beijing, 2013.
36. A. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703-4832
37. X.-M. Zeng, Chem. Rev. 2013, 113, 6864-6900.
38. J. Marco-Contelles, M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2857-2899
39. K. H. Altmann, Org. Biomol. Chem. 2004, 2, 2137-2152
40. K. Miyashita, T. Imanishi, Chem. Rev. 2005, 105, 4515-4536
41. J. Kobayashi, T. Kubota, J. Nat. Prod. 2007, 70, 451-460
42. Z.-L. Zhou, Y.-X. Yang, J. Ding, Y.-C. Li, Z.-H. Miao, Nat. Prod. Rep. 2012, 29, 457-475.
43. Y.-G. Zhu, Q. Wang, R. G. Cornwall, Y. Shi, Chem. Rev. 2014, 114, 8199-8256
44. R. L. Davis, J. Stiller, T. Naicker, H. Jiang, K. A. Jørgensen, Angew. Chem. Int. Ed. 2014, 53, 7406-7426
45. Angew. Chem. 2014, 126, 7534-7556
46. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976.
47. Y. Nishikawa, H. Yamamoto, J. Am. Chem. Soc. 2011, 133, 8432-8435
48. Y. Chu, X. Liu, W. Li, X. Hu, L. Lin, X. Feng, Chem. Sci. 2012, 3, 1996-2000.
49. T. Yamazaki, T. Ichige, T. Kitazume, Org. Lett. 2004, 6, 4073-4076
50. M. Shimizu, T. Fujimoto, H. Minezaki, T. Hata, T. Hiyama, J. Am. Chem. Soc. 2001, 123, 6947-6948.
51. S. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2013, 52, 4312-4348
52. Angew. Chem. 2013, 125, 4408-4445.
53. H. Kawai, S. Okusu, Z. Yuan, E. Tokunaga, A. Yamano, M. Shiro, N. Shibata, Angew. Chem. Int. Ed. 2013, 52, 2221-2225
54. Angew. Chem. 2013, 125, 2277-2281.
55. S.-X. Wu, D. Pan, C.-Y. Cao, Q. Wang, F.-X. Chen, Adv. Synth. Catal. 2013, 355, 1917-1923.
56. C. Schneider, Angew. Chem. Int. Ed. 2002, 41, 744-746
57. Angew. Chem. 2002, 114, 771-772
58. Y. Wang, R. L. Tennyson, D. Romo, Heterocycles 2004, 64, 605.
59. K. Hirano, I. Piel, F. Glorius, Adv. Synth. Catal. 2008, 350, 984-988
60. Y. Li, Z.-A. Zhao, H. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 1885-1890
61. C. Burstein, F. Glorius, Angew. Chem. Int. Ed. 2004, 43, 6205-6208
62. Angew. Chem. 2004, 116, 6331-6334.
63. W. J. Linn, US patent 3271419, 1966.
64. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655
65. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2988-3000
66. Angew. Chem. 2007, 119, 3046-3058.
67. X.-N. Wang, P.-L. Shao, H. Lv, S. Ye, Org. Lett. 2009, 11, 4029-4031.
68. M. L. Quan, C. D. Ellis, A. Y. Liauw, R. S. Alexander, R. M. Knabb, G. Lam, M. R. Wright, P. C. Wong, R. R. Wexler, J. Med. Chem. 1999, 42, 2760-2773
69. V. Kumar, R. Aggarwal, S. P. Singh, J. Fluorine Chem. 2006, 127, 880-888.
70. T. Mita, Y. Kudo, T. Mizukoshi, H. Hotta, K. Maeda, S. Takii, WO2004018410, 2004
71. M. Yaosaka, T. Utsunomiya, Y. Moriyama, T. Matsumoto, K. Matoba, WO2009001942, 2009
72. T. Mita, T. Kikuchi, T. Mizukoshi, M. Yaosaka, M. Komoda, WO2005085216, 2005
73. W. Zambach, P. Renold, WO2009049846, 2009
74. P. Renold, W. Zambach, P. Maienfisch, M. Muehlebach, WO2009080250, 2009
75. T. Murata, Y. Yoneta, J. Mihara, K. Domon, M. Hatazawa, K. Araki, E. Shimojo, K. Shibuya, T. Ichihara, U. Goergens, A. Voerste, A. Becker, E. Franken, K. Mueller, WO2009112275, 2009.
76. K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909.
77. H. Kawai, K. Tachi, E. Tokunaga, M. Shiro, N. Shibata, Angew. Chem. Int. Ed. 2011, 50, 7803-7806
78. Angew. Chem. 2011, 123, 7949-7952.
79. K. Matoba, H. Kawai, T. Furukawa, A. Kusuda, E. Tokunaga, S. Nakamura, M. Shiro, N. Shibata, Angew. Chem. Int. Ed. 2010, 49, 5762-5766
80. Angew. Chem. 2010, 122, 5898-5902.
81. M. J. Raihan, V. Kavala, P. M. Habib, Q.-Z. Guan, C.-W. Kuo, C.-F. Yao, J. Org. Chem. 2011, 76, 424-434.
82. H. Kawai, S. Okusu, E. Tokunaga, N. Shibata, Eur. J. Org. Chem. 2013, 6506-6509.
83. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
84. D.-S. Wang, Z.-S. Ye, Q.-A. Chen, Y.-G. Zhou, C.-B. Yu, H.-J. Fan, Y. Duan, J. Am. Chem. Soc. 2011, 133, 8866-8869
85. Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660-5661
86. X.-Y. Han, F.-R. Zhong, Y.-Q. Wang, Y.-X. Lu, Angew. Chem. Int. Ed. 2012, 51, 767-770
87. Angew. Chem. 2012, 124, 791-794
88. C. E. Henry, Q.-H. Xu, Y.-C. Fan, T. J. Martin, L. Belding, T. Dudding, O. Kwon, J. Am. Chem. Soc. 2014, 136, 11890-11893.
89. T. Murata, M. Ataka, Y. Yoneta, H. Watanabe, E. Shimojo, K. Shibuya, T. Ichihara, PCT Int. Appl. WO 2011054871, 2011
90. H. Ihara, K. Kumamoto, PCT Int. Appl. WO 2010090344, 2010
91. T. Mita, E. Ikeda, H. Takahashi, M. Komoda, PCT Int. Appl. WO 2009072621, 2009.
92. H. Kawai, T. Kitayama, E. Tokunaga, T. Matsumoto, H. Sato, M. Shiro, N. Shibata, Chem. Commun. 2012, 48, 4067-4069.
93. O. Marrec, C. Christophe, T. Billard, B. Langlois, J.-P. Vors, S. Pazenok, Adv. Synth. Catal. 2010, 352, 2825-2830.
94. S. Kobayashi, T. Tsubogo, S. Saito, Y. Yamashita, Org. Lett. 2008, 10, 807-809
95. T. Ma, X. Fu, C. W. Kee, L. Zong, Y. Pan, K.-W. Huang, C.-H. Tan, J. Am. Chem. Soc. 2011, 133, 2828-2831.
96. H. Kawai, Y. Sugita, E. Tokunaga, H. Sato, M. Shiro, N. Shibata, Chem. Commun. 2012, 48, 3632-3634.
97. J.-R. Gao, H. Wu, B. Xiang, W.-B. Yu, L. Han, Y.-X. Jia, J. Am. Chem. Soc. 2013, 135, 2983-2986
98. Q. Chen, G.-Q. Wang, X.-X. Jiang, Z.-Q. Xu, L. Lin, R. Wang, Org. Lett. 2014, 16, 1394-1397
99. H. Wu, R.-R. Liu, Y.-X. Jia, Synlett 2014, 25, 457-460.
100. H. Kawai, S. Okusu, E. Tokunaga, H. Sato, M. Shiro, N. Shibata, Angew. Chem. Int. Ed. 2012, 51, 4959-4962
101. Angew. Chem. 2012, 124, 5043-5046.
102. H. Kawai, Z. Yuan, T. Kitayama, E. Tokunaga, N. Shibata, Angew. Chem. Int. Ed. 2013, 52, 5575-5579
103. Angew. Chem. 2013, 125, 5685-5689.
104. D. O'Hagan, Nat. Prod. Rep. 1997, 14, 637-651
105. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446.
106. B. Engels, M. Christl, Angew. Chem. Int. Ed. 2009, 48, 7968-7970
107. Angew. Chem. 2009, 121, 8110-8112
108. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887-2902
109. M. Álvarez-Corral, M. Munoz-Dorado, I. Rodriguez-Garcia, Chem. Rev. 2008, 108, 3174-3198
110. W. Zeng, G.-Y. Chen, Y.-G. Zhou, Y.-X. Li, J. Am. Chem. Soc. 2007, 129, 750-751
111. L. He, X.-H. Chen, D.-N. Wang, S.-W. Luo, W.-Q. Zhang, J. Yu, L. Ren, L.-Z. Gong, J. Am. Chem. Soc. 2011, 133, 13504-13518
112. C.-J. Wang, G. Liang, Z.-Y. Xue, F. Gao, J. Am. Chem. Soc. 2008, 130, 17250-17251
113. Y. Yamashita, X.-X. Guo, R. Takashita, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 3262-3263.
114. Q.-H. Li, M.-C. Tong, J. Li, H.-Y. Tao, C.-J. Wang, Chem. Commun. 2011, 47, 11110-11112.
115. B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963-983
116. P. de Armas, D. Tejedor, F. Garcia-Tellado, Angew. Chem. Int. Ed. 2010, 49, 1013-1016
117. Angew. Chem. 2010, 122, 1029-1032.
118. Q.-Q. Min, C.-Y. He, H. Zhou, X. Zhang, Chem. Commun. 2010, 46, 8029-8031
119. G. Huang, J. Yang, X. Zhang, Chem. Commun. 2011, 47, 5587-5589.
120. G.-C. Huang, Z.-S. Yin, X.-G. Zhang, Chem. Eur. J. 2013, 19, 11992-11998.
121. M. T. Corbett, Q.-H. Xu, J. S. Johnson, Org. Lett. 2014, 16, 2362-2365.
122. Goodman and Gilman's the Pharmacological Basis of Therapeutics, 10th ed. (Eds.:, J. G. Hardman, L. E. Limbird, G. A. Gilman,), McGraw-Hill, New York, 2001, Section III.
123. R. J. Sundberg, Indoles, Academic Press, New York, 1996
124. E. Marqués-Lõpez, R. P. Herrera, M. Christmann, Nat. Prod. Rep. 2010, 27, 1138-1167.
125. J. Alemán, A. Milelli, S. Cabrera, E. Reys, K. A. Jørgensen, Chem. Eur. J. 2008, 14, 10958-10966
126. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175
127. Angew. Chem. 2004, 116, 5248-5286.
128. C.-H. Ma, T.-R. Kang, L. He, Q.-Z. Liu, Eur. J. Org. Chem. 2014, 3981-3985.
129. X. Shen, W. Zhang, C. Ni, Y. Gu, J. Hu, J. Am. Chem. Soc. 2012, 134, 16999-17002
130. J. Sun, D. Shi, M. Ma, S. Li, S. Wang, L. Han, Y. Yang, X. Fan, J. Shi, L. He, J. Nat. Prod. 2005, 68, 915-919.
131. K. Futatsugi, H. Yamamoto, Angew. Chem. Int. Ed. 2005, 44, 1484-1487
132. Angew. Chem. 2005, 117, 1508-1511
133. K. Shibatomi, K. Futatsugi, F. Kobayashi, S. Iwasa, H. Yamamoto, J. Am. Chem. Soc. 2010, 132, 5625-5627.
134. K. Shibatomi, F. Kobayashi, A. Narayama, I. Fujisawa, S. Iwasa, Chem. Commun. 2012, 48, 413-415.
135. X.-Q. Dong, J.-W. Sun, Org. Lett. 2014, 16, 2450-2453.
136. P. Chauhan, S. Mahajan, D. Enders, Chem. Rev. 2014, 114, 8807-8864
137. X.-Q. Dong, X. Fang, C.-J. Wang, Org. Lett. 2011, 13, 4426-4429
138. J. Tang, D.-Q. Xu, A.-B. Xia, Y.-F. Wang, J.-R. Jiang, S.-P. Luo, Z.-Y. Xu, Adv. Synth. Catal. 2010, 352, 2121-2126
139. S.-W. Duan, Y. Li, Y.-Y. Liu, Y.-Q. Zou, D.-Q. Shi, W.-J. Xiao, Chem. Commun. 2012, 48, 5160-5162.
140. Y. Su, J.-B. Ling, S. Zhang, P.-F. Xu, J. Org. Chem. 2013, 78, 11053-11058.
141. L. Tan, C.-Y. Chen, R. Tillyer, E. J. J. Grabowski, P. J. Reider, Angew. Chem. Int. Ed. 1999, 38, 711-713
142. Angew. Chem. 1999, 111, 724-727
143. L. Tan, C.-Y. Chen, Enantiomer 1999, 4, 599-608
144. C.-Y. Chen, R. D. Richard, L. Tan, PCT Int. Appl., WO 9851676, 1998.
145. K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768
146. T. Kawasaki, Y. Matsumura, T. Tsutsumi, K. Suzuki, M. Ito, K. Soai, Science 2009, 324, 492-495.
147. N. Chinkov, A. Warm, E. M. Carreira, Angew. Chem. Int. Ed. 2011, 50, 2957-2961
148. Angew. Chem. 2011, 123, 3014-3018.
149. S. Mizuta, N. Shibata, S. Akiti, H. Fujimoto, S. Nakamura, T. Toru, Org. Lett. 2007, 9, 3707-3710.
150. H. Kawai, T. Kitayama, E. Tokunaga, N. Shibata, Eur. J. Org. Chem. 2011, 5959-5961.
151. S. Okusu, H. Kawai, Y. Yasuda, Y. Sugita, T. Kitayama, E. Tokunaga, N. Shibata, Asian J. Org. Chem. 2014, 3, 449-452.
152. H. L. Yale, M. Kalkstein, J. Med. Chem. 1967, 10, 334-336
153. J. I. Levin, P. S. Chan, T. Bailey, A. S. Katocs, A. M. Venkatesan, Bioorg. Med. Chem. Lett. 1994, 4, 1141-1146.
154. G. S. Kauffman, G. D. Harris, R. L. Dorow, B. R. P. Stone, R. L. Parsons, Jr., J. A. Pesti, N. A. Magnus, J. M. Fortunak, P. N. Confalone, W. A. Nugent, Org. Lett. 2000, 2, 3119-3121.
155. B. Jiang, Y.-G. Si, Angew. Chem. Int. Ed. 2004, 43, 216-218
156. Angew. Chem. 2004, 116, 218-220.
157. L. Mengozzi, A. Gualandi, P. G. Cozzi, Chem. Sci. 2014, 5, 3915-3921.
158. B. Jiang, J.-J. Dong, Y.-G. Si, X.-L. Zhao, Z.-G. Huang, M. Xu, Adv. Synth. Catal. 2008, 350, 1360-1366.
159. N. R. Amarasinghe, P. Turner, M. H. Todd, Adv. Synth. Catal. 2012, 354, 2954-2958
160. A. Parra, R. Alfaro, L. Marzo, A. Moreno-Carrasco, J. L. G. Ruano, J. Aleman, Chem. Commun. 2012, 48, 9759-9761.
161. H.-X. Xie, Y.-N. Zhang, S.-L. Zhang, X.-B. Chen, W. Wang, Angew. Chem. Int. Ed. 2011, 50, 11773-11776
162. Angew. Chem. 2011, 123, 11977-11980.
163. Y.-D. Shao, S.-K. Tian, Chem. Commun. 2012, 48, 4899-4901.
164. F.-G. Zhang, X.-Y. Zhu, S. Li, J. Nie, J.-A. Ma, Chem. Commun. 2012, 48, 11552-11554.
165. H.-X. Xie, A.-G. Song, X.-X. Song, X.-S. Zhang, W. Wang, Tetrahedron Lett. 2013, 54, 1409-1411.
166. S. Nakamura, Org. Biomol. Chem. 2014, 12, 394-405.
167. H.-N. Yuan, S. Wang, J. Nie, W. Meng, Q.-W. Yao, J.-A. Ma, Angew. Chem. Int. Ed. 2013, 52, 3869-3873
168. Angew. Chem. 2013, 125, 3961-3965.
169. H.-N. Yuan, S. Li, J. Nie, Y. Zheng, J.-A. Ma, Chem. Eur. J. 2013, 19, 15856-15860.
170. F.-G. Zhang, H. Ma, Y. Zheng, J.-A. Ma, Tetrahedron 2012, 68, 7663-7669.
171. F.-G. Zhang, H. Ma, J. Nie, Y. Zheng, Q.-Z. Gao, J.-A. Ma, Adv. Synth. Catal. 2012, 354, 1422-1428.
172. D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557-2590.
173. Y. Duan, X.-Y. Zhu, J.-A. Ma, Y.-G. Zhou, Tetrahedron Lett. 2013, 54, 6161-6163.
174. Z.-R. He, Y.-Y. Huang, V. Francis, Acta Chim. Sin. 2013, 71, 700-712.
175. D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047-9153
176. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004, 43, 1566-1568
177. Angew. Chem. 2004, 116, 1592-1594
178. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5375.
179. K.-F. Zhang, J. Nie, R. Guo, Y. Zheng, J.-A. Ma, Adv. Synth. Catal. 2013, 355, 3497-3502.
180. J. G. Allen, F. R. Atherton, M. J. Hall, C. H. Hassal, S. W. Holmes, R. W. Lambert, L. J. Nisbet, P. S. Ringrose, Nature 1978, 272, 56-58
181. F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem. 1986, 29, 29-40.
182. H.-X. Xie, A.-G. Song, X.-S. Zhang, X.-B. Chen, H. Li, C.-Q. Sheng, W. Wang, Chem. Commun. 2013, 49, 928-930.
183. L. C. Morrill, A. D. Smith, Chem. Soc. Rev. 2014, 43, 6214-6226.
184. J. Wang, H. Li, H.-X. Xie, L.-S. Zu, X. Shen, W. Wang, Angew. Chem. Int. Ed. 2007, 46, 9050-9053
185. Angew. Chem. 2007, 119, 9208-9211.
186. P. Li, Z. Chai, S.-L. Zhao, Y.-Q. Yang, H.-F. Wang, C.-W. Zheng, Y.-P. Cai, G. Zhao, S.-Z. Zhu, Chem. Commun. 2009, 7369-7371.
187. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
188. L.-L. Wen, Q.-L. Shen, L. Lu, Org. Lett. 2010, 12, 4655-4657.
189. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766-771
190. J. Dugal-Tessier, E. A. O'Bryan, T. B. H. Schroeder, D. T. Cohen, K. A. Scheidt, Angew. Chem. Int. Ed. 2012, 51, 4963-4967
191. Angew. Chem. 2012, 124, 5047-5051.
192. J.-M. Mo, X.-K. Chen, Y.-R. Chi, J. Am. Chem. Soc. 2012, 134, 8810-8813.
193. H. U. Vora, P. Wheeler, T. Rovis, Adv. Synth. Catal. 2012, 354, 1617-1639
194. J. Douglas, G. Churchill, A. D. Smith, Synthesis 2012, 44, 2295-2309.
195. A. T. Davies, J. E. Taylor, J. Douglas, C. J. Collett, L. C. Morrill, C. Fallan, A. M. Z. Slawin, G. Churchill, A. D. Smith, J. Org. Chem. 2013, 78, 9243-9257.
196. A. T. Davies, P. M. Pickett, A. M. Z. Slawin, A. D. Smith, ACS Catal. 2014, 4, 2696-2700.
197. D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin, A. D. Smith, J. Am. Chem. Soc. 2011, 133, 2714-2720.
198. L. C. Morrill, J. Douglas, T. Lebl, A. M. Z. Slawin, D. J. Fox, A. D. Smith, Chem. Sci. 2013, 4, 4146-4155.
199. G. Atul, J. R. Vishnu, Tetrahedron 2009, 65, 7865-7913
200. J. Mahatthananchai, A. M. Dumas, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 10954-10990
201. Angew. Chem. 2012, 124, 11114-11152.
202. A. Sanz-Marco, A. García-Ortiz, G. Blay, J. R. Pedro, Chem. Commun. 2014, 50, 2275-2278.
203. A. R. Mattocks, The Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, London, 1986
204. A. D. Elbein, R. J. Molyneux, in Alkaloids: Chemical and Biological Perspectives (Ed.:, S. W. Pelletier,), Wiley, New York, 1987.
205. Y.-Y. Huang, E. Tokunaga, S. Suzuki, M. Shiro, N. Shibata, Org. Lett. 2010, 12, 1136-1138.
206. S. Ogawa, N. Shibata, J. Inagaki, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. Int. Ed. 2007, 46, 8666-8669
207. Angew. Chem. 2007, 119, 8820-8823.
208. S. Ogawa, N. Iida, E. Tokunaga, M. Shiro, N. Shibata, Chem. Eur. J. 2010, 16, 7090-7095.
209. C. Ratsch, A. Hofmann, The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications, Park Street Press, Vermont, 2005.
210. L.-L. Wen, Q.-L. Shen, X.-L. Wang, L. Lu, J. Org. Chem. 2011, 76, 2282-2285.
211. C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017
212. F. Rondu, G. L. Bihan, X. Wang, A. Lamouri, E. Touboul, G. Dive, T. Bellahsene, B. Pfeiffer, P. Renard, B. Guardiola-Lamaitre, D. Manechez, L. Penicaud, A. Ktorza, J. J. Godfroid, J. Med. Chem. 1997, 40, 3793-3803
213. Y. Hsiao, L. S. Hegedus, J. Org. Chem. 1997, 62, 3586-3591.
214. M.-X. Zhao, H.-L. Bi, R.-H. Jiang, X.-W. Xu, M. Shi, Org. Lett. 2014, 16, 4566-4569.
215. D. Cahard, V. Bizet, Chem. Soc. Rev. 2014, 43, 135-147.
216. G. K. S. Prakash, F. Wang, Z. Zhang, R. Haiges, M. Rahm, K. O. Christe, T. Mathew, G. A. Olah, Angew. Chem. Int. Ed. 2014, 53, 11575-11578
217. Angew. Chem. 2014, 126, 11759-11762.