Axially chiral N-heterocyclic carbene gold(I) complex catalyzed asymmetric cycloisomerization of 1,6-enynes

Organometallics

Volumn 30, Issue 14, 2011, Pages 3859-3869

  Wang, Wenfeng ^a   Yang, Jinming ^a   Wang, Feijun ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,6-ENYNES; CHIRAL N-HETEROCYCLIC CARBENES; COORDINATION GEOMETRY; CYCLOISOMERIZATIONS; OPTICALLY ACTIVE; OXIDATIVE REARRANGEMENTS; SPECTROSCOPIC DATA; X-RAY DIFFRACTION STUDIES;

ALDEHYDES; CARBON INORGANIC COMPOUNDS; CATALYSIS; CATALYSTS; COORDINATION REACTIONS; DIFFRACTIVE OPTICS; ENANTIOSELECTIVITY; GOLD; ORGANIC COMPOUNDS; SINGLE CRYSTALS; X RAY DIFFRACTION;

GOLD COMPOUNDS;

EID: 79960537823     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2004404     Document Type: Article

References (81)

1. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403
2. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211
3. Jimémez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333-346
4. Fürster, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449
5. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754-6756
6. Duschek, A.; Kirsch, S. F. Angew. Chem., Int. Ed. 2008, 47, 5703-5705
7. Bongers, N.; Krause, N. Angew. Chem., Int. Ed. 2008, 47, 2178-2181
8. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265
9. Arcadi, A. Chem. Rev. 2008, 108, 3266-3325
10. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350
11. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378
12. Shapiro, N. D.; Toste, F. D. Synlett 2010, 2010, 675-691
13. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406
14. For recent reviews, see: Widenhoefer, R. A. Chem.-Eur. J. 2008, 14, 5382-5391
15. Sengupta, S.; Shi, X. D. ChemCatChem 2010, 2, 609-619, and refs 1g and 1h
16. Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002-18003
17. LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453
18. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496-499
19. Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. Org. Lett. 2007, 9, 2887-2889
20. Zhang, Z.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2007, 46, 283-285
21. Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148-14149
22. Kleinbeck, F.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 9178-9179
23. Tarselli, M. A.; Chianese, A. R.; Lee, S. J.; Gagne, M. R. Angew. Chem., Int. Ed. 2007, 46, 6670-6673
24. Luzung, M. R.; Mauleon, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402-12403
25. Alonso, I.; Trillo, B.; Lopez, F.; Montserrat, S.; Ujaque, G.; Castedo, L.; Lledos, A.; Mascarenas, J. L. J. Am. Chem. Soc. 2009, 131, 13020-13030
26. Gonzalez, A. Z.; Toste, F. D. Org. Lett. 2010, 12, 200-203
27. Munoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293-1300
28. Chao, C. M.; Genin, E.; Toullec, P. Y.; Genêt, J. P.; Michelet, V. J. Organomet. Chem. 2009, 694, 538-545
29. Chao, C. M.; Vitale, M. R.; Toullec, P. Y.; Genêt, J. P.; Michelet, V. Chem.-Eur. J. 2009, 15, 1319-1323
30. Chao, C. M.; Beltrami, D.; Toullec, P. Y.; Michelet, V. Chem. Commun. 2009, 6988-6990
31. Hashmi, A. S. K.; Hamzic, M.; Rominger, F.; Bats, J. W. Chem.-Eur. J. 2009, 15, 13318-13322
32. Wilckens, K.; Uhlemann, M.; Czekelius, C. Chem.-Eur. J. 2009, 15, 13323-13326
33. Matsumoto, Y.; Selim, K. B.; Nakanishi, H.; Yamada, K.; Yamamoto, Y.; Tomioka, K. Tetrahedron Lett. 2010, 51, 404-406
34. A recent alternative approach of employing chiral counteranions is very attractive for conducting asymmetric gold catalysis; see ref 4c and Hashmi, A. S. K. Nature 2007, 449, 292-293
35. For selected books and reviews on NHC ligands, see: Nolan, S. P., Ed. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
36. Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer: Berlin, 2007.
37. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91
38. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
39. Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951-961
40. Kirmse, W. Angew. Chem., Int. Ed. 2004, 43, 1767-1769
41. Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636
42. Douthwaite, R. E. Coord. Chem. Rev. 2007, 251, 702-717
43. Kühl, O. Chem. Soc. Rev. 2007, 36, 592-607
44. Kantchev, E. A. B.; OBrien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813
45. Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
46. Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181-222
47. Weskamp, T.; Bohm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22
48. Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50-64
49. Strassner, T. Top. Organomet. Chem. 2004, 13, 1-20
50. Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem. 2005, 690, 5407-5413
51. Crabtree, R. H. J. Organomet. Chem. 2005, 690, 5451-5457
52. Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883
53. For the other attempted asymmetric transformations with chiral NHC-Au catalysts, see ref 6f and Corberán, R.; Ramírez, J.; Poyatos, M.; Peris, E.; Fernández, E. Tetrahedron: Asymmetry 2006, 17, 1759-1762
54. de Fremont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411-2418 For reviews on [(NHC)Au] complexes, see: Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776-1782
55. Raubenheimer, H. G.; Cronje, S. Chem. Soc. Rev. 2008, 37, 1998-2011
56. Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561-3598
57. Duan, W. L.; Shi, M.; Rong, G. B. Chem. Commun. 2003, 2916-2917
58. Xu, Q.; Duan, W. L.; Lei, Z. Y.; Zhu, Z. B.; Shi, M. Tetrahedron 2005, 61, 11225-11229
59. Chen, T.; Jiang, J. J.; Xu, Q.; Shi, M. Org. Lett. 2007, 9, 865-868
60. Zhang, T.; Shi, M. Chem.-Eur. J. 2008, 14, 3759-3764
61. Ma, G. N.; Zhang, T.; Shi, M. Org. Lett. 2009, 11, 875-878
62. Wang, W. F.; Zhang, T.; Shi, M. Organometallics 2009, 28, 2640-2642
63. Liu, Z.; Shi, M. Tetrahedron 2010, 66, 2619-2623
64. Liu, Z.; Shi, M. Organometallics 2010, 29, 2831-2834
65. Xu, Q.; Zhang, R.; Zhang, T.; Shi, M. J. Org. Chem. 2010, 75, 3935-3937
66. Zhang, R.; Xu, Q.; Zhang, X.; Zhang, T.; Shi, M. Tetrahedron: Asymmetry 2010, 21, 1928-1935
67. Liu, Z.; Gu, P.; Shi, M.; McDowell, P.; Li, G. Org. Lett. 2011, 13, 2314-2317
68. w: 0.0448, 0.1129.
69. Zhang, T.; Liu, S. J.; Shi, M.; Zhao, M. X. Synthesis 2008, 17, 2819-2824
70. Wang, W. F.; Zhang, T.; Wang, F. J.; Shi, M. Tetrahedron 2011, 67, 1523-1529
71. w: 0.0635, 0.1464.
72. w: 0.0406, 0.0790.
73. The absolute stereochemistries of 53a and 53b were assigned by analogy to compound 54 followed by comparison of the sign of optical rotation of 54 with that in the literature: Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genet, J. P. Chem. Commun. 2004, 850-851
74. Porcel, S.; Echavarren, A. M. Angew. Chem., Int. Ed. 2007, 46, 2672-2676
75. Nieto-Oberhuber, C.; Munoz, M. P.; Lopez, S.; Jimenez-Nunez, E.; Nevado, C.; Herrero-Gomez, E.; Raducan, M.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 1677-1693
76. For references on trapping of cyclypropylcarbenes, see: Nieto-Oberhuber, C.; Lopez, S.; Munoz, M. P.; Jimenez-Nunez, E.; Bunuel, E.; Cardenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 1694-1702
77. Lopez, S.; Herrero-Gomez, E.; Perez-Galan, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 6029-6032
78. Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838-5839
79. Perez-Galan, P.; Herrero-Gomez, E.; Hog, D. T.; Martin, N. J. A.; Maseras, F.; Echavarren, A. M. Chem. Sci. 2011, 2, 141-149
80. For recent discussions on gold-stabilized carbocations rather than carbenes, see: Fürster, A.; Morency, L. Angew. Chem., Int. Ed. 2008, 47, 5030-5033
81. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754-6756