Asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides: Enantioselective introduction of functionalized diarylmethine stereogenic centers

Angewandte Chemie - International Edition

Volumn 52, Issue 35, 2013, Pages 9229-9233

  Chu, Wen Dao ^a   Zhang, Le Fen ^a   Bao, Xu ^a   Zhao, Xian He ^a   Zeng, Chao ^a   Du, Ji Yuan ^a   Zhang, Guo Biao ^a   Wang, Fang Xin ^a   Ma, Xiao Yan ^a   Fan, Chun An ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

arenes; asymmetric catalysis; enantioselectivity; phase transfer catalysis; quinone methides

Indexed keywords

1 ,6-CONJUGATE ADDITIONS; ALTERNATIVE ROUTES; ARENES; ASYMMETRIC CATALYSIS; PHASE TRANSFER CATALYSIS; QUINONE METHIDES; REACTION SEQUENCES; STEREOGENIC CENTERS;

CATALYSIS;

ENANTIOSELECTIVITY;

ALKANE; CINCHONA ALKALOID; INDOLE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; QUINONE METHIDE;

ARENES; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENANTIOSELECTIVITY; PHASE-TRANSFER CATALYSIS; QUINONE METHIDES; STEREOISOMERISM; SYNTHESIS;

ARENES; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; PHASE-TRANSFER CATALYSIS; QUINONE METHIDES;

ALKANES; CATALYSIS; CINCHONA ALKALOIDS; INDOLEQUINONES; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM;

EID: 84882949882     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303928     Document Type: Article

References (106)

1. A. B. Turner, Q. Rev. Chem. Soc. 1964, 18, 347
2. "Quinone Methides":, H.-U. Wagner, R. Gompper, in The Chemistry of the Quinonoid Compounds, Vol.2 (Ed.:, S. Patai,), Wiley, New York, 1974, chap. 18, pp. 1145-1178
3. M. G. Peter, Angew. Chem. 1989, 101, 572
4. Angew. Chem. Int. Ed. Engl. 1989, 28, 555
5. T. Itoh, Prog. Polym. Sci. 2001, 26, 1019
6. Quinone Methides (Ed.:, S.E. Rokita,), Wiley, Hoboken, 2009
7. M. M. Toteva, J. P. Richard, Adv. Phys. Org. Chem. 2011, 45, 39.
8. A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 1903, 36, 2792.
9. K.-i. Takao, T. Sasaki, T. Kozaki, Y. Yanagisawa, K.-i. Tadano, A. Kawashima, H. Shinonaga, Org. Lett. 2001, 3, 4291
10. B. E. Barragán-Huerta, J. Peralta-Cruz, R. F. González- Laredo, J. Karchesy, Phytochemistry 2004, 65, 925
11. H. J. Martin, T. Magauer, J. Mulzer, Angew. Chem. 2010, 122, 5746
12. Angew. Chem. Int. Ed. 2010, 49, 5614
13. R. Jansen, K. Gerth, H. Steinmetz, S. Reinecke, W. Kessler, A. Kirschning, R. Müller, Chem. Eur. J. 2011, 17, 7739.
14. A. A. Larsen, Nature 1969, 224, 25
15. D. Hamels, P. M. Dansette, E. A. Hillard, S. Top, A. Vessières, P. Herson, G. Jaouen, D. Mansuy, Angew. Chem. 2009, 121, 9288
16. Angew. Chem. Int. Ed. 2009, 48, 9124
17. G. B. Messiano, T. daSilva, I. R. Nascimento, L. M. X. Lopes, Phytochemistry 2009, 70, 590
18. R. Dehn, Y. Katsuyama, A. Weber, K. Gerth, R. Jansen, H. Steinmetz, G. Höfle, R. Müller, A. Kirschning, Angew. Chem. 2011, 123, 3968
19. Angew. Chem. Int. Ed. 2011, 50, 3882
20. C. Sridar, J. D'Agostino, P. F. Hollenberg, Drug Metab. Dispos. 2012, 40, 2280.
21. P. Wan, B. Barker, L. Diao, M. Fischer, Y. Shi, C. Yang, Can. J. Chem. 1996, 74, 465
22. Y. Chiang, A. J. Kresge, Y. Zhu, Pure Appl. Chem. 2000, 72, 2299
23. R. W. VanDeWater, T. R. R. Pettus, Tetrahedron 2002, 58, 5367
24. H. Amouri, J. LeBras, Acc. Chem. Res. 2002, 35, 501
25. S. B. Ferreira, F. de C. daSilva, A. C. Pinto, D. T. G. Gonzaga, V. F. Ferreira, J. Heterocycl. Chem. 2009, 46, 1080
26. T. P. Pathak, M. S. Sigman, J. Org. Chem. 2011, 76, 9210
27. N. J. Willis, C. D. Bray, Chem. Eur. J. 2012, 18, 9160, and references therein.
28. D. J. Hart, P. A. Cain, D. A. Evans, J. Am. Chem. Soc. 1978, 100, 1548
29. S. R. Angle, K. D. Turnbull, J. Am. Chem. Soc. 1989, 111, 1136
30. S. R. Angle, M. S. Louie, H. L. Mattson, W. Yang, Tetrahedron Lett. 1989, 30, 1193
31. S. R. Angle, J. D. Rainier, J. Org. Chem. 1992, 57, 6883
32. S. R. Angle, D. O. Arnaiz, J. P. Boyce, R. P. Frutos, M. S. Louie, H. L. Mattson-Arnaiz, J. D. Rainier, K. D. Turnbull, W. Yang, J. Org. Chem. 1994, 59, 6322
33. S. R. Angle, T. Wada, Tetrahedron Lett. 1997, 38, 7955
34. B. C. Raju, P. Neelakantan, U. T. Bhalerao, Tetrahedron Lett. 2004, 45, 7487.
35. S. R. Angle, D. O. Arnaiz, J. Org. Chem. 1990, 55, 3708
36. S. R. Angle, D. O. Arnaiz, J. Org. Chem. 1992, 57, 5937
37. W. Baik, H. J. Lee, C. H. Yoo, J. W. Jung, B. H. Kim, J. Chem. Soc. Perkin Trans. 1 1997, 587
38. W. Baik, H. J. Lee, S. Koo, B. H. Kim, Tetrahedron Lett. 1998, 39, 8125
39. S. Kim, Y. Kitano, M. Tada, K. Chiba, Tetrahedron Lett. 2000, 41, 7079
40. W. Baik, H. J. Lee, J. M. Jang, S. Koo, B. H. Kim, J. Org. Chem. 2000, 65, 108.
41. N. Nakagaki, T. Uno, M. Kubo, T. Itoh, J. Polym. Sci. Part A 2009, 47, 5923
42. S. Lizuka, N. Nakagaki, T. Uno, M. Kubo, T. Itoh, Macromolecules 2010, 43, 6962
43. R. Nakagawa, T. Uno, M. Kubo, T. Itoh, Polym. Bull. 2012, 68, 1831
44. T. Nagai, T. Uno, M. Kubo, T. Itoh, J. Polym. Sci. Part A 2012, 50, 466.
45. A. G. Csákÿ, G. deLaHerrán, M. C. Murcia, Chem. Soc. Rev. 2010, 39, 4080
46. A. T. Biju, ChemCatChem 2011, 3, 1847
47. E. M. P. Silva, A. M. S. Silva, Synthesis 2012, 3109, and references therein.
48. P. Mauleõn, J. C. Carretero, Org. Lett. 2004, 6, 3195
49. J.-F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850
50. J.-F. Paquin, C. R. J. Stephenson, C. Defieber, E. M. Carreira, Org. Lett. 2005, 7, 3821
51. T. Nishikata, Y. Yamamoto, I. D. Gridnev, N. Miyaura, Organometallics 2005, 24, 5025
52. N. Tokunaga, T. Hayashi, Tetrahedron: Asymmetry 2006, 17, 607
53. T. Itoh, T. Mase, T. Nishikata, T. Iyama, H. Tachikawa, Y. Kobayashi, Y. Yamamoto, N. Miyaura, Tetrahedron 2006, 62, 9610
54. T. Nishikata, Y. Yamamoto, N. Miyaura, Adv. Synth. Catal. 2007, 349, 1759
55. T. Nishikata, Y. Yamamoto, N. Miyaura, Tetrahedron Lett. 2007, 48, 4007
56. S. Sörgel, N. Tokunaga, K. Sasaki, K. Okamoto, T. Hayashi, Org. Lett. 2008, 10, 589
57. Z.-Q. Wang, C.-G. Feng, S.-S. Zhang, M.-H. Xu, G.-Q. Lin, Angew. Chem. 2010, 122, 5916
58. Angew. Chem. Int. Ed. 2010, 49, 5780
59. Y.-X. Liao, C.-H. Xing, M. Israel, Q.-S. Hu, Org. Lett. 2011, 13, 2058
60. H. M. Turner, J. Patel, N. Niljianskul, J. M. Chong, Org. Lett. 2011, 13, 5796
61. F. Lang, G. Chen, L. Li, J. Xing, F. Han, L. Cun, J. Liao, Chem. Eur. J. 2011, 17, 5242
62. T. Nishimura, A. Noishiki, T. Hayashi, Chem. Commun. 2012, 48, 973
63. F. Xue, D. Wang, X. Li, B. Wan, J. Org. Chem. 2012, 77, 3071
64. G. Chen, J. Xing, P. Cao, J. Liao, Tetrahedron 2012, 68, 5908.
65. K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2001, 113, 164
66. Angew. Chem. Int. Ed. 2001, 40, 160
67. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894
68. H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2007, 119, 6608
69. Angew. Chem. Int. Ed. 2007, 46, 6488
70. T.-Y. Liu, H.-L. Cui, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Chem. Commun. 2007, 2228
71. H. Zhang, Y.-H. Liao, W.-C. Yuan, X.-M. Zhang, Eur. J. Org. Chem. 2010, 3215
72. Y. Sohtome, B. Shin, N. Horitsugi, R. Takagi, K. Noguchi, K. Nagasawa, Angew. Chem. 2010, 122, 7457
73. Angew. Chem. Int. Ed. 2010, 49, 7299.
74. P. Tolstoy, M. Engman, A. Paptchikhine, J. Bergquist, T. L. Church, A. W.-M. Leung, P. G. Andersson, J. Am. Chem. Soc. 2009, 131, 8855
75. X. Wang, A. Guram, S. Caille, J. Hu, J. P. Preston, M. Ronk, S. Walker, Org. Lett. 2011, 13, 1881
76. E. Spahn, A. Albright, M. Shevlin, L. Pauli, A. Pfaltz, R. E. Gawley, J. Org. Chem. 2013, 78, 2731
77. E. N. Bess, M. S. Sigman, Org. Lett. 2013, 15, 646.
78. R. Shintani, K. Takatsu, M. Takeda, T. Hayashi, Angew. Chem. 2011, 123, 8815
79. Angew. Chem. Int. Ed. 2011, 50, 8656
80. S. M. Podhajsky, Y. Iwai, A. Cook-Sneathen, M. S. Sigman, Tetrahedron 2011, 67, 4435
81. Y. Luan, S. E. Schaus, J. Am. Chem. Soc. 2012, 134, 19965.
82. M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3
83. K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013
84. M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506
85. B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518
86. J. Vachon, J. Lacour, Chimia 2006, 60, 266
87. T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300
88. Angew. Chem. Int. Ed. 2007, 46, 4222
89. T. Ooi, K. Maruoka, Aldrichimica Acta 2007, 40, 77
90. T. Hashimoto, K. Maruoka, Chem. Rev. 2007, 107, 5656
91. K. Maruoka, Org. Process Res. Dev. 2008, 12, 679
92. S.-s. Jew, H.-g. Park, Chem. Commun. 2009, 7090
93. K. Maruoka, Chem. Rec. 2010, 10, 254
94. S. Shirakawa, K. Maruoka, Angew. Chem. 2013, 125, 4408
95. Angew. Chem. Int. Ed. 2013, 52, 4312.
96. M. J. O'Donnell, S. Wu, I. Esikova, A. Mi, WO 9506029, 1995; For 4 b, see
97. M. J. O'Donnell, F. Delgado, C. Hostettler, R. Schwesinger, Tetrahedron Lett. 1998, 39, 8775; For 4 c, see
98. T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 9539; For 4 d, see
99. T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 4724
100. Angew. Chem. Int. Ed. 2002, 41, 4542; For 4 e, see
101. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139; For 4 f, see
102. K. Maruoka, WO 2005073196, 2005.
103. CCDC931906 (3 da) and 931907 (3 qa) 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.
104. S. A. Saleh, H. I. Tashtoush, Tetrahedron 1998, 54, 14157.
105. E. W. Colvin, in Silicon Reagents in Organic Synthesis Academic Press, 1988
106. The Chemistry of Organic Silicon Compounds (Eds.:, S. Patai, Z. Rappoport,), Wiley, New York, 1989.