Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides

Chemical Communications

Volumn 51, Issue 12, 2015, Pages 2320-2323

  Jia, Minqiang ^a   Monari, Magda ^a   Yang, Qing Qing ^a   Bandini, Marco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENAMIDE DERIVATIVE; AMIDE; CYCLOBUTANE DERIVATIVE; GOLD; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ELECTROPHILICITY; ENANTIOSELECTIVITY; HYDROGENATION; LOW TEMPERATURE; NUCLEOPHILICITY; STEREOCHEMISTRY; CHEMISTRY; CONFORMATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

AMIDES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; GOLD; INDOLES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84921892283     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc08736d     Document Type: Article

References (96)

1. (a) S. B. Jones, B. Simmons, A. Mastracchio and D. W. C. MacMillan, Nature, 2011, 475, 183;
2. (b) C. W. Wright, Nat. Prod. Rep., 2010, 27, 961;
3. (c) M. Zhang, X. Huang, L. Shen and Y. Qin, J. Am. Chem. Soc., 2009, 131, 6013;
4. (d) W. Zi, W. Xie and D. Ma, J. Am. Chem. Soc., 2012, 134, 9126;
5. (e) B. D. Horning and D. W. C. MacMillan, J. Am. Chem. Soc., 2013, 135, 6442;
6. (f) J. M. Smith, J. Moreno, B. W. Boal and N. K. Garg, J. Am. Chem. Soc., 2014, 136, 4504.
7. (a) D. B. Grotjahn and K. P. C. Vollhardt, J. Am. Chem. Soc., 1986, 108, 2091;
8. (b) C. Ferrer, C. H. M. Amijs and A. E. Echavarren, Chem. - Eur. J., 2007, 13, 1358.
9. (c) F. López Ortiz, M. J. Iglesias, I. Fernández, C. M. Andúljar Sánchez and G. R. Gómez, Chem. Rev., 2007, 107, 1580;
10. (d) L. Pouységu, D. Deffieux and S. Quideau, Tetrahedron, 2010, 66, 2235;
11. (e) S. P. Roche and J. A. Porco Jr, Angew. Chem., Int. Ed., 2011, 50, 4068;
12. (f) C.-X. Zhuo, W. Zhang and S.-L. You, Angew. Chem., Int. Ed., 2012, 51, 12662;
13. (g) C. C. J. Loh and D. Enders, Angew. Chem., Int. Ed., 2012, 51, 46;
14. (h) C.-X. Zhuo, C. Zheng and S.-L. You, Acc. Chem. Res., 2014, 47, 2558.
15. (a) O. Lozano, G. Blessley, T. Martinez del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman and V. Gouverneur, Angew. Chem., Int. Ed., 2011, 50, 8105;
16. (b) Q. Cai, C. Zheng, J.-W. Zhang and S.-L. You, Angew. Chem., Int. Ed., 2012, 51, 8665;
17. (c) Q. Cai and S.-L. You, Org. Lett., 2012, 14, 3040;
18. (d) Q. Cai, C. Liu, X.-W. Liang and S.-L. You, Org. Lett., 2012, 14, 4588;
19. (e) W. Xie, G. Jiang, H. Liu, J. Hu, X. Pan, H. Zhang, X. Wan, Y. Lai and D. Ma, Angew. Chem., Int. Ed., 2013, 52, 12924;
20. ( f ) M. E. Kieffer, K. V. Chuang and S. E. Reisman, J. Am. Chem. Soc., 2013, 135, 5557;
21. (g) H. Liu, G. Jiang, X. Pan, X. Wan, Y. Lai, D. Ma and W. Xie, Org. Lett., 2014, 16, 1908.
22. (a) J. Barluenga, E. Tudela, A. Ballesteros and M. Tomás, J. Am. Chem. Soc., 2009, 131, 2096;
23. (b) L. M. Repka, J. Ni and S. E. Reisman, J. Am. Chem. Soc., 2010, 132, 14418;
24. (c) Y. Lian and H. M. L. Davies, J. Am. Chem. Soc., 2010, 132, 440;
25. (d) G. Özüduru, T. Schubach and M. M. K. Boysen, Org. Lett., 2012, 14, 4990;
26. (e) J. E. Spangler and H. M. L. Davies, J. Am. Chem. Soc., 2013, 135, 6802;
27. (f) J. Huang, L. Zhao, Y. Liu, W. Cao and X. Wu, Org. Lett., 2013, 15, 4338;
28. (g) H. Xiong, H. Xu, S. Liao, Z. Xie and Y. Tang, J. Am. Chem. Soc., 2013, 135, 7851;
29. (h) H. Wang and S. E. Reisman, Angew. Chem., Int. Ed., 2014, 53, 6206.
30. (i) J. Zhang, Z. Chen, H.-H. Wu and J. Zhang, Chem. Commun., 2012, 48, 1817;
31. (j) M. Kawano, T. Kiuchi, S. Negishi, H. Tanaka, T. Hoshikawa, J. Matsuo and H. Ishibashi, Angew. Chem., Int. Ed., 2013, 52, 906;
32. (k) H. Li, R. P. Hughes and J. Wu, J. Am. Chem. Soc., 2014, 136, 6288.
33. (a) G.-J. Duan, J.-B. Ling, W.-P. Wang, Y.-C. Luo and P.-F. Xu, Chem. Commun., 2013, 49, 4625;
34. (b) W. R. Gutekunst and P. S. Baran, J. Org. Chem., 2014, 79, 2430.
35. (a) L. Zhang, J. Am. Chem. Soc., 2005, 127, 16804;
36. (b) H. Faustino, P. Bernal, L. Castedo, F. López and J. L. Mascareñas, Adv. Synth. Catal., 2012, 354, 1658.
37. (a) R. L. LaLonde, W. E. Brenzovich Jr., D. Benitez, E. Tkatchouk, K. Kelley, W. A. Goddard III and F. D. Toste, Chem. Sci., 2010, 1, 226;
38. (b) T. de Haro and C. Nevado, Synthesis, 2011, 2530;
39. (c) M. Bandini, Chem. Soc. Rev., 2011, 40, 1358;
40. (d) M. Rudolph and A. S. K. Hashmi, Chem. Soc. Rev., 2012, 41, 2448;
41. (e) M. Livendahl and A. M. Echavarren, Chim. Oggi, 2012, 30, 19;
42. (f) E. M. Barreiro, L. A. Adrio, K. K. Hii and J. B. Brazier, Eur. J. Org. Chem., 2013, 1027;
43. (g) A. Fürstner, Acc. Chem. Res., 2014, 8, 925;
44. (h) C. Obradors and A. M. Echavarren, Acc. Chem. Res., 2014, 8, 902;
45. Y.-M. Wang, A. D. Lackner and F. D. Toste, Acc. Chem. Res., 2014, 8, 889;
46. (j ) W. Yang and A. S. K. Hashmi, Chem. Soc. Rev., 2014, 43, 2941;
47. (k) N. Bongers and N. Krause, Angew. Chem., Int. Ed., 2008, 47, 2178;
48. R. A. Widenhoefer, Chem. - Eur. J., 2008, 14, 5382;
49. S. Sengupta and X. Shi, ChemCatChem, 2010, 2, 609;
50. (n) A. Pradal, P. Y. Toullec and V. Michelet, Synthesis, 2011, 1501;
51. (o) N. T. Patil, Chem. - Asian J., 2012, 7, 2186;
52. (p) G. Cera and M. Bandini, Isr. J. Chem., 2013, 53, 848.
53. [2+1] (a) M. J. Johansson, D. J. Gorin, S. T. Staben and F. D. Toste, J. Am. Chem. Soc., 2005, 127, 18002;
54. (b) I. D. G. Watson, S. Ritter and F. D. Toste, J. Am. Chem. Soc., 2009, 131, 2056;
55. J. F. Briones and H. M. L. Davies, J. Am. Chem. Soc., 2012, 134, 11916;
56. Z.-Y. Cao, X. Wang, C. Tan, X.-L. Zhao, J. Zhou and K. Ding, J. Am. Chem. Soc., 2013, 135, 8197. [4+3]
57. (e) I. Alonso, H. Faustino, D. López and J. L. Mascareñas, Angew. Chem., Int. Ed., 2011, 50, 11496;
58. (f) D. Garayalde, K. Krüger and C. Nevado, Angew. Chem., Int. Ed., 2011, 50, 911. [3+2]
59. (g) J. F. Briones and H. M. L. Davies, J. Am. Chem. Soc., 2013, 135, 13314;
60. (h) G.-H. Li, W. Zhou, X.-X. Li, Q.-W. Bi, Z. Wang, Z.-G. Zhao, W.-X. Hu and Z. Chen, Chem. Commun., 2013, 49, 4770. [4+2]
61. I. Alonso, B. Trillo, F. López, S. Montserrat, G. Ujaque, L. Castedo, A. Lledós and J. L. Mascareñas, J. Am. Chem. Soc., 2009, 131, 13020;
62. (j) A. Z. González and F. D. Toste, Org. Lett., 2010, 12, 200;
63. (k) J. Francos, F. Grande-Carmona, H. Faustino, J. Iglesias-Sigüenza, E. Diez, I. Alonso, R. Fernández, J. M. Lassaletta, F. López and J. L. Mascareñas, J. Am. Chem. Soc., 2012, 134, 14322;
64. S. Montserrat, H. A. Faustino, J. L. Mascareñas, F. López and G. Ujaque, Chem. - Eur. J., 2013, 19, 15248. [3+3]
65. Z.-M. Zhang, P. Chen, W. Li, Y. Niu, X.-L. Zhao and J. Zhang, Angew. Chem., Int. Ed., 2014, 53, 4350.
66. (n) H. Faustino, I. Alonso, J. L. Mascareñas and F. López, Angew. Chem., Int. Ed., 2013, 52, 6526.
67. (o) B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Soc. Rev., 2010, 39, 783;
68. (p) F. López and J. L. Mascareñas, Beilstein J. Org. Chem., 2011, 7, 1075;
69. (q) F. López and J. L. Mascareñas, Beilstein J. Org. Chem., 2013, 9, 2250.
70. (a) M. R. Luzung, P. Mauleón and F. D. Toste, J. Am. Chem. Soc., 2007, 129, 12402;
71. (b) H. Teller, S. Flügge, R. Goddard and A. Fürstner, Angew. Chem., Int. Ed., 2010, 49, 1949;
72. A. Z. González, D. Benitez, E. Tkatchouk, W. A. Goddard, III and F. D. Toste, J. Am. Chem. Soc., 2011, 133, 5500;
73. S. Suárez-Pantiga, C. Hernández-Díaz, E. Rubio and J. M. González, Angew. Chem., Int. Ed., 2012, 51, 11552;
74. (e) H. Teller, M. Corbet, L. Mantilli, G. Gopakumar, R. Goddard, W. Thiel and A. Fürstner, J. Am. Chem. Soc., 2012, 134, 15331;
75. (f) S. Suárez-Pantiga, C. Hernández-Díaz, M. Piedrafita, E. Rubio and J. M. Gonzáles, Adv. Synth. Catal., 2012, 354, 1651;
76. (g) P. Maulón, ChemCatChem, 2013, 5, 2149;
77. (h) X.-X. Li, L.-L. Zhu, W. Zhou and Z. Chen, Org. Lett., 2012, 14, 436;
78. H. Zheng, R. J. Felix and M. R. Gagné, Org. Lett., 2014, 16, 2272.
79. (a) M. Bandini and A. Eichholzer, Angew. Chem., Int. Ed., 2009, 48, 9608;
80. (b) M. Bandini and A. Eichholzer, Angew. Chem., Int. Ed., 2009, 48, 9533;
81. M. Bandini, M. Monari, A. Romaniello and M. Tragni, Chem. - Eur. J., 2010, 16, 14272;
82. M. Bandini, A. Gualandi, M. Monari, A. Romaniello, D. Savoia and M. Tragni, J. Organomet. Chem., 2011, 696, 338;
83. (e) G. Cera, P. Crispino, M. Monari and M. Bandini, Chem. Commun., 2011, 47, 7803;
84. (f) G. Cera, S. Piscitelli, M. Chiarucci, G. Fabrizi, A. Goggiamani, R. S. Ramón, S. P. Nolan and M. Bandini, Angew. Chem., Int. Ed., 2012, 51, 9891;
85. (g) G. Cera, M. Chiarucci, A. Mazzanti, M. Mancinelli and M. Bandini, Org. Lett., 2012, 14, 1350;
86. (h) M. Chiarucci, E. Matteucci, G. Cera, G. Fabrizi and M. Bandini, Chem. - Asian J., 2013, 8, 1776;
87. M. Chiarucci, R. Mocci, L.-D. Syntrivanis, G. Cera, A. Mazzanti and M. Bandini, Angew. Chem., Int. Ed., 2013, 52, 10850;
88. (j) M. Jia, G. Cera, D. Perrotta, M. Monari and M. Bandini, Chem. - Eur. J., 2014, 20, 9875;
89. (k) C. Romano, M. Jia, M. Monari, E. Manoni and M. Bandini, Angew. Chem., Int. Ed., 2014, 53, 13854.
90. (a) L.-L. Wei, H. Xiong and R. P. Hsung, Acc. Chem. Res., 2003, 36, 773;
91. (b) T. Lu, Z. Lu, Z.-X. Ma, Y. Zhang and R. P. Hsung, Chem. Rev., 2013, 113, 4862.
92. S. Montserrat, H. Faustino, A. Lledos, J. L. Mascareñas, F. López and G. Ujaque, Chem. - Eur. J., 2013, 19, 15248.
93. For a complete list of screened reaction parameters see the ESI.† A scope limitation on the allenamide was recorded, with 2a being the only allenamide enabling the present [2+2]-cycloaddition.
94. Catalyst loadings of 2.5 or 5.0 mol% (referred to the L4) were alternatively used in order to optimize reaction rates.
95. V. Pirovano, L. Decataldo, E. Rossi and R. Vicente, Chem. Commun., 2013, 49, 3594.
96. 16 Cambridge Crystallographic Data Centre (http://www.ccdc.cam.ac.uk) under the accession code CCDC 1009450.