Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes

Angewandte Chemie - International Edition

Volumn 54, Issue 41, 2015, Pages 12149-12152

  Dieckmann, Michael ^a   Jang, Yun Suk ^a   Cramer, Nicolai ^a  

^a EPFL   (Switzerland)

Author keywords

asymmetric catalysis; cycloisomerization; cyclopentadienyl ligands; enantioselectivity; iridium

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; IRIDIUM; ISOMERIZATION; LIGANDS; METAL COMPLEXES; PROPANE; SCAFFOLDS; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

ASYMMETRIC CATALYSIS; BEARING MEMBERS; CYCLOISOMERIZATION REACTIONS; CYCLOISOMERIZATIONS; CYCLOPENTADIENYL LIGANDS; CYCLOPENTADIENYLS; ENANTIOSELECTIVE; PROOF OF CONCEPT;

IRIDIUM COMPOUNDS;

EID: 84942823400     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506483     Document Type: Article

References (73)

1. J. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, 2010.
2. R. L. Halterman, K. P. C. Vollhardt, M. E. A. Welker, J. Am. Chem. Soc. 1987, 109, 8105-8107
3. S. L. Colletti, R. L. Halterman, Organometallics 1991, 10, 3438-3448
4. Z. Chen, R. L. Halterman, Synlett 1990, 103-104
5. S. L. Colletti, R. L. Halterman, Tetrahedron Lett. 1989, 30, 3513-3516
6. Z. Li, A. Vasella, Helv. Chim. Acta 1996, 79, 2201-2218
7. R. L. Halterman, L. D. Crow, Tetrahedron Lett. 2003, 44, 2907-2909.
8. R. L. Haltermann, Chem. Rev. 1992, 92, 965-994
9. R. L. Halterman, K. P. C. Vollhardt, Organometallics 1988, 7, 883-892
10. R. L. Halterman, K. P. C. Vollhardt, Tetrahedron Lett. 1986, 27, 1461-1464
11. C. Krüger, R. Goddard, M. Nolte, J. Organomet. Chem. 1993, 459, 107-115
12. A. Gutnov, B. Heller, H.-J. Drexler, A. Spannenberg, G. Oehme, Organometallics 2003, 22, 1550-1553
13. H. Schumann, O. Stenzel, S. Dechert, F. Girgsdies, J. Blum, D. Gelman, R. L. Halterman, Eur. J. Inorg. Chem. 2002, 211-219
14. A. Gutnov, H.-J. Drexler, A. Spannenberg, G. Oehme, B. Heller, Organometallics 2004, 23, 1002-1009
15. G. P. McGlacken, C. T. O'Brien, A. C. Whitwood, I. J. S. Fairlamb, Organometallics 2007, 26, 3722-3728
16. Z. R. Turner, J.-C. Buffet, D. O'Hare, Organometallics 2014, 33, 3891-3903
17. R. Laï, J.-C. Daran, D. Nuel, M. Sanz, N. Summerton, N. Vanthuyne, A. Zaragori-Benedetti, Dalton Trans. 2013, 42, 7980-7990
18. B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sundermann, Chem. Eur. J. 2007, 13, 1117-1128
19. A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, Angew. Chem. Int. Ed. 2004, 43, 3795-3797
20. Angew. Chem. 2004, 116, 3883-3886.
21. B. Ye, N. Cramer, Science 2012, 338, 504-506
22. B. Ye, N. Cramer, J. Am. Chem. Soc. 2013, 135, 636-639.
23. B. Ye, N. Cramer, Acc. Chem. Res. 2015, 48, 1308-1318
24. B. Ye, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 7896-7899
25. Angew. Chem. 2014, 126, 8030-8033
26. M. D. Wodrich, B. Ye, J. F. Gonthier, C. Corminboeuf, N. Cramer, Chem. Eur. J. 2014, 20, 15409-15418
27. B. Ye, P. A. Donets, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 507-511
28. Angew. Chem. 2014, 126, 517-521
29. J. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2014, 53, 13244-13247
30. Angew. Chem. 2014, 126, 13460-13463
31. J. Zheng, S.-B. Wang, C. Zheng, S.-L. You, J. Am. Chem. Soc. 2015, 137, 4880-4883
32. B. Ye, N. Cramer, Synlett 2015, 26, 1490-1495
33. G. Y. Song, W. N. O. Wiley, Z. M. Hou, J. Am. Chem. Soc. 2014, 136, 12209-12212.
34. D. Bellus, S. V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost, in Science of Synthesis-Methods of Molecular Transformations, Vol. 1, (Ed. , M. Lautens,), Wiley, New York, 2001.
35. C. White, A. Yates, P. M. Maitlis, Inorg. Synth. 1992, 29, 228-234.
36. D. M. Heinekey, J. M. Millar, T. K. Koetzle, N. G. Payne, K. W. Zilm, J. Am. Chem. Soc. 1990, 112, 909-919.
37. E. Benedetti, A. Simonneau, A. Hours, H. Amouri, A. Penoni, G. Palmisano, M. Malacria, J.-P. Goddard, L. Fensterbank, Adv. Synth. Catal. 2011, 353, 1908-1912.
38. A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410-3449
39. Angew. Chem. 2007, 119, 3478-3519.
40. I. D. G. Watson, F. D. Toste, Chem. Sci. 2012, 3, 2899-2919
41. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296
42. R. Dorel, A. M. Echavarren, J. Org. Chem. 2015, DOI: 10.1021/acs.joc.5b01106.
43. A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863-11869
44. F. Schröder, C. Tugny, E. Salanouve, H. Clavier, L. Giordano, D. Moraleda, Y. Gimbert, V. Mouriès-Mansuy, J.-P. Goddard, L. Fensterbank, Organometallics 2014, 33, 4051-4056
45. D.-H. Zhang, Y. Wei, M. Shi, Chem. Eur. J. 2012, 18, 7026-7029
46. J. B. Xia, W.-B. Liu, T.-M. Wang, S.-L. You, Chem. Eur. J. 2010, 16, 6442-6446
47. S. Anjum, J. Marco-Contelles, Tetrahedron 2005, 61, 4793-4803
48. J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569
49. K. Fourmy, S. Mallet-Ladeira, O. Dechy-Cabaret, M. Gouygou, Dalton Trans. 2014, 43, 6728-6734
50. E. Soriano, P. Ballesteros, J. Marco-Contelles, J. Org. Chem. 2004, 69, 8018-8023
51. N. M. Groome, E. E. Elboray, M. W. Inman, H. A. Dondas, R. M. Phillips, C. Kilner, R. Grigg, Chem. Eur. J. 2013, 19, 2180-2184.
52. S. Son, S. Y. Kim, ChemistryOpen 2012, 1, 169-172
53. K. Ota, S. I. Lee, J.-M. Tang, M. Takachi, H. Nakai, T. Morimoto, H. Sakurai, K. Kataoka, N. Chatani, J. Am. Chem. Soc. 2009, 131, 15203-15211
54. S. Y. Kim, J. Org. Chem. 2010, 75, 1281-1284
55. N. Chatani, H. Inoue, T. Morimoto, T. Muto, S. Murai, J. Org. Chem. 2001, 66, 4433-4436
56. S. M. Stevenson, E. T. Newcomb, E. M. Ferreira, Chem. Commun. 2014, 50, 5239-5241
57. S. H. Sim, J. H. Park, Y. K. Chung, Adv. Synth. Catal. 2010, 352, 317-322
58. H. M. Oh, J. E. Park, J. Kim, J. H. Kim, Y. K. Kang, Y. K. Chung, Chem. Eur. J. 2014, 20, 9024-9036
59. J. Böhmer, R. Grigg, J. D. Marchbank, Chem. Commun. 2002, 768-769.
60. T. Shibata, Y. Kobayashi, S. Maekawa, N. Toshida, K. Takagi, Tetrahedron 2005, 61, 9018-9024
61. M. Barbazanges, M. Augé, J. Moussa, H. Amouri, C. Aubert, C. Desmartes, L. Fensterbank, V. Gandon, M. Malacria, C. Ollivier, Chem. Eur. J. 2011, 17, 13789-13794.
62. A. Pradal, C.-M. Chao, P. Y. Toullec, V. Michelet, Beilstein J. Org. Chem. 2011, 7, 1021-1029
63. K. Yavari, P. Aillard, Y. Zhang, F. Nutter, P. Retailleau, A. Voituriez, A. Marinetti, Angew. Chem. Int. Ed. 2014, 53, 861-865
64. Angew. Chem. 2014, 126, 880-884
65. P. Pérez-Galán, E. Herrero-Gõmez, D. T. Hog, N. J. A. Martin, F. Maseras, A. M. Echavarren, Chem. Sci. 2011, 2, 141-149
66. H. Teller, M. Corbet, L. Mantilli, G. Gopakumar, R. Goddard, W. Thiel, A. Fürstner, J. Am. Chem. Soc. 2012, 134, 15331-15342
67. W. Wang, J. Yang, F. Wang, M. Shi, Organometallics 2011, 30, 3859-3869.
68. D. Brissy, M. Skander, H. Jullien, P. Retailleau, A. Marinetti, Org. Lett. 2009, 11, 2137-2139
69. D. Brissy, M. Skander, P. Retailleau, G. Frison, A. Marinetti, Organometallics 2009, 28, 140-151.
70. T. Nishimura, Y. Maeda, T. Hayashi, Org. Lett. 2011, 13, 3674-3677
71. T. Nishimura, Y. Takiguchi, Y. Maeda, T. Hayashi, Adv. Synth. Catal. 2013, 355, 1374-1382
72. K. Matsutomi, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2014, 136, 7626-7630.
73. V. S. Sridevi, W. Y. Fan, W. K. Leong, Organometallics 2007, 26, 1173-1177.