Gold(I)-catalyzed cascade cycloadditions between allenamides and carbonyl-tethered alkenes: An enantioselective approach to oxa-bridged medium-sized carbocycles

Angewandte Chemie - International Edition

Volumn 52, Issue 25, 2013, Pages 6526-6530

  Faustino, Hélio ^a   Alonso, Isaac ^a   Mascareñas, José L ^a   Lõpez, Fernando ^a,b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

annulation; cascade reactions; enantioselective; gold; homogeneous catalysis

Indexed keywords

ANNULATION; CASCADE REACTIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE APPROACH; GOLD CATALYSTS; HIGH ENANTIOSELECTIVITY; HOMOGENEOUS CATALYSIS; PHOSPHORAMIDITES;

CATALYSTS; CYCLOADDITION; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS;

GOLD;

EID: 84878927202     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302713     Document Type: Article

References (76)

1. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
2. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
3. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221
4. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
5. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994-2009.
6. D. Garayalde, C. Nevado, ACS Catal. 2012, 2, 1462-1479
7. F. Lõpez, J. L. Mascareñas, Beilstein J. Org. Chem. 2011, 7, 1075-1094
8. I. D. G. Watson, F. D. Toste, Chem. Sci. 2012, 3, 2899-2919
9. S. Bhunia, R. S. Liu, Pure. Appl. Chem. 2012, 84, 1749-1757.
10. B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, Chem. Eur. J. 2009, 15, 3336-3339
11. I. Alonso, B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, J. Am. Chem. Soc. 2009, 131, 13020-13030
12. I. Alonso, H. Faustino, F. Lõpez, J. L. Mascareñas, Angew. Chem. 2011, 123, 11698-11702
13. Angew. Chem. Int. Ed. 2011, 50, 11496-11500
14. P. Mauleõn, R. M. Zeldin, A. Z. González, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6348-6349
15. A. Z. González, D. Benitez, E. Tkatchouk, W. A. Goddard, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 5500-5507
16. X. Huang, L. Zhang, J. Am. Chem. Soc. 2007, 129, 6398-6399
17. M. R. Luzung, P. Mauleõn, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12402-12403
18. M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem. 2010, 122, 2596-2600
19. Angew. Chem. Int. Ed. 2010, 49, 2542-2546
20. A. K. Gupta, C. Y. Rhim, C. H. Oh, R. S. Mane, S. H. Han, Green Chem. 2006, 8, 25-28
21. R. Chaudhuri, H. Y. Liao, R. S. Liu, Chem. Eur. J. 2009, 15, 8895-8901.
22. H. Faustino, F. Lõpez, L. Castedo, J. L. Mascareñas, Chem. Sci. 2011, 2, 633-637
23. J. Francos, F. Grande-Carmona, H. Faustino, J. Iglesias-Sigüenza, E. Diez, I. Alonso, R. Fernández, J. M. Lassaletta, F. Lõpez, J. L. Mascareñas, J. Am. Chem. Soc. 2012, 134, 14322-14325; for a related reaction using allenyl ethers, see
24. Q. R. Wang, G. A. Wang, Y. Zou, Z. M. Li, A. Goeke, Adv. Synth. Catal. 2011, 353, 550-556.
25. H. Faustino, P. Bernal, L. Castedo, F. Lõpez, J. L. Mascareñas, Adv. Synth. Catal. 2012, 354, 1658-1664
26. X.-X. Li, L.-L. Zhu, W. Zhou, Z. Chen, Org. Lett. 2012, 14, 1185-1185
27. S. Suárez-Pantiga, C. Hernández-Díaz, M. Piedrafita, E. Rubio, J. M. González, Adv. Synth. Catal. 2012, 354, 1651-1657
28. S. Suárez-Pantiga, C. Hernández-Díaz, E. Rubio, J. M. González, Angew. Chem. 2012, 124, 11720-11723
29. Angew. Chem. Int. Ed. 2012, 51, 11552-11555.
30. The use of allenamides appears critical, probably because the amide group facilitates the activation of the allene, while stabilizing the resulting cationic intermediates. For a recent review on allenamides, see: T. Lu, Z. Lu, Z.-X. Ma, Y. Zhang, R. P. Hsung, Chem. Rev. 2013, DOI:.
31. C. Obradors, A. M. Echavarren, Chem. Eur. J. 2013, 19, 3547-3551; for work of the same group on intramolecular cycloisomerizations of oxoenynes, see
32. N. Huguet, A. M. Echavarren, Synlett 2012, 49-53
33. A. Escribano-Cuesta, V. Lõpez-Carrillo, D. Janssen, A. M. Echavarren, Chem. Eur. J. 2009, 15, 5646-5650
34. E. Jiménez-Núñez, C. K. Claverie, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 5578-5581
35. Angew. Chem. Int. Ed. 2006, 45, 5452-5455
36. K. Molawi, N. Delpont, A. M. Echavarren, Angew. Chem. 2010, 122, 3595-3597
37. Angew. Chem. Int. Ed. 2010, 49, 3517-3519
38. E. Jiménez-Núñez, K. Molawi, A. M. Echavarren, Chem. Commun. 2009, 7327-7329; see also
39. M. Schelwies, R. Moser, A. L. Dempwolff, F. Rominger, G. Helmchen, Chem. Eur. J. 2009, 15, 10888-10900
40. D. B. Huple, R. S. Liu, Chem. Commun. 2012, 48, 10975-10977.
41. N. Z. Burns, M. R. Witten, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 14578-14581
42. K. Ishida, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2010, 132, 8842-8843
43. J. Huang, R. P. Hsung, J. Am. Chem. Soc. 2005, 127, 50-51
44. M. Harmata, S. K. Ghosh, X. C. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058-2059; for selected enantiospecific and chiral-auxiliary-based approaches to these systems, see
45. I. V. Hartung, H. M. R. Hoffmann, Angew. Chem. 2004, 116, 1968-1984
46. Angew. Chem. Int. Ed. 2004, 43, 1934-1949
47. B. Li, Y. J. Zhao, Y. C. Lai, T. P. Loh, Angew. Chem. 2012, 124, 8165-8169
48. Angew. Chem. Int. Ed. 2012, 51, 8041-8045
49. B. Lo, S. Lam, W.-T. Wong, P. Chiu, Angew. Chem. 2012, 124, 12286-12289
50. Angew. Chem. Int. Ed. 2012, 51, 12120-12123
51. F. Peng, D. G. Hall, J. Am. Chem. Soc. 2007, 129, 3070-3071
52. M. Harmata, Adv. Synth. Catal. 2006, 348, 2297-2306
53. F. Lõpez, L. Castedo, J. L. Mascareñas, Org. Lett. 2002, 4, 3683-3685.
54. C. M. Yu, J. Y. Lee, B. So, J. Hong, Angew. Chem. 2002, 114, 169-171
55. Angew. Chem. Int. Ed. 2002, 41, 161-163
56. F. Lõpez, L. Castedo, J. L. Mascareñas, Org. Lett. 2005, 7, 287-290; enantioselective approaches to any type of eight-membered ring are also virtually unknown, see
57. I. D. G. Watson, S. Ritter, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 2056-2057
58. B. DeBoef, W. R. Counts, S. R. Gilbertson, J. Org. Chem. 2007, 72, 799-804
59. R. T. Yu, R. K. Friedman, T. Rovis, J. Am. Chem. Soc. 2009, 131, 13250-13251.
60. Z. X. Yu, Y. Wang, Y. Y. Wang, Chem. Asian J. 2010, 5, 1072-1088
61. L. Yet, Chem. Rev. 2000, 100, 2963-3008
62. G. Mehta, V. Singh, Chem. Rev. 1999, 99, 881-930
63. M. A. Winnik, Chem. Rev. 1981, 81, 491-524
64. N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757-5821; see also
65. D. G. I. Kingston, J. Org. Chem. 2008, 73, 3975
66. R. S. Daum, S. Kar, P. Kirkpatrick, Nat. Rev. Drug Discovery 2007, 6, 865-866.
67. G. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95-102
68. C. Galli, L. Mandolini, Eur. J. Org. Chem. 2000, 3117-3125.
69. G. A. Molander, Acc. Chem. Res. 1998, 31, 603-609
70. F. Lõpez, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2002, 124, 4218-4219
71. J. R. Rodríguez, L. Castedo, J. L. Mascareñas, Chem. Eur. J. 2002, 8, 2923-2930; for a review, see
72. F. Lõpez, J. L. Mascareñas, Chem. Eur. J. 2007, 13, 2172-2178; for Au-catalyzed formal cycloadditions that afford oxa-bridged medium-sized rings, see
73. Y. Bai, W. J. Tao, J. Ren, Z. W. Wang, Angew. Chem. 2012, 124, 4188-4192
74. Angew. Chem. Int. Ed. 2012, 51, 4112-4116
75. T.-M. Teng, A. Das, D. B. Huple, R.-S. Liu, J. Am. Chem. Soc. 2010, 132, 12565-12567.
76. V. Michelet, A. Pradal, P. Y. Toullec, Synthesis 2011, 1501-1514.