Chiral gold complex-catalyzed hetero-diels-alder reaction of diazenes: Highly enantioselective and general for dienes

Journal of the American Chemical Society

Volumn 135, Issue 9, 2013, Pages 3323-3326

  Liu, Bin ^a   Li, Kang Nan ^a   Luo, Shi Wei ^a   Huang, Jian Zhou ^a   Pang, Huan ^a   Gong, Liu Zhu ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOISOMERIZATIONS; DIAZENES; DIENOPHILES; ENANTIOSELECTIVE; GOLD CATALYSTS; GOLD COMPLEXES; HETERO-DIELS-ALDER REACTIONS; LEWIS ACID;

CATALYSIS; ENANTIOSELECTIVITY; GOLD; UREA;

GOLD COMPOUNDS;

GOLD COMPLEX; LEWIS ACID;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ISOMERIZATION;

ALKADIENES; CATALYSIS; IMIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; STEREOISOMERISM;

EID: 84874923106     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3110472     Document Type: Article

References (51)

1. The Diels-Alder Reaction: Selected Practical Methods; Fringuelli, F., Taticchi, A., Eds.; John Wiley & Sons: New York, 2002.
2. Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 151-209.
3. Comprehensive Asymmetric Catalysis III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 1237-1254.
4. Gouverneur, V.; Reiter, M. Chem.-Eur. J. 2005, 11, 5806
5. Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558
6. Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1
7. Pellissier, H. Tetrahedron 2009, 65, 2839
8. Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Synlett 2007, 14, 2147
9. Yamamoto, H.; Kawasaki, M. Bull. Chem. Soc. Jpn. 2007, 80, 595
10. Alves, M. J.; Costa, F. T.; Duarte, V. C.; Fortes, A. G.; Martins, J. A.; Micaelo, N. M. J. Org. Chem. 2011, 76, 9584
11. Moreno-Clavijo, E.; Carmona, A. T.; Moreno-Vargas, A. J.; álvarez, E.; Robina, I. Synlett 2010, 9, 1367
12. Moreno-Clavijo, E.; Carmona, A. T.; Moreno-Vargas, A. J.; Rodríguez-Carvajal, M. A.; Robina, I. Bioorg. Med. Chem. 2010, 18, 4648
13. Li, W.-H.; Gan, J.-G.; Ma, D.-W. Angew. Chem., Int. Ed. 2009, 48, 8891
14. Phillip Kennedy, J.; Brogan, J. T.; Lindsley, C. W. Tetrahedron Lett. 2008, 49, 4116
15. Chapman, S. K.; Glant, S. K. J. Pharm. Sci. 1980, 69, 733
16. Ducep, J. B.; Heintzelmann, B.; Jund, K.; Lesur, B.; Schleimer, M.; Zimmermann, P. R. Tetrahedron: Asymmetry 1997, 8, 327
17. Oscarsson, K.; Oscarson, S.; Vrang, L.; Hamelink, E.; Hallberg, A.; Samuelsson, B. Bioorg. Med. Chem. 2003, 11, 1235
18. Zuccarello, G.; Bouzide, A.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Brisander, M.; Danielsson, H.; Nillroth, U.; Karlén, A.; Hallberg, A.; Classon, B.; Samuelsson, B. J. Org. Chem. 1998, 63, 4898
19. Aburel, P. S.; Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 2344
20. Kawasaki, M.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 16482
21. Windenhoefer, R. A. Chem.-Eur. J. 2008, 14, 5382
22. Sengupta, S.; Shi, X.-D. ChemCatChem 2010, 2, 609
23. Pradal, A.; Toullec, P. Y.; Michelet, V. Synthesis 2011, 10, 1501
24. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405
25. For a example that gold(I) complex unified both σ- or π-Lewis acid properties, see: Boiaryna, L.; El Mkaddem, M. K.; Taillier, C.; Dalla, V.; Othman, M. Chem.-Eur. J. 2012, 18, 14192
26. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
27. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
28. Arcadi, A. Chem. Rev. 2008, 108, 3266
29. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
30. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
31. Martín-Rodríguez, M.; Nájera, C.; Sansano, J. M.; de Cózar, A.; Cossío, F. P. Chem.-Eur. J. 2011, 17, 14224
32. Jagdale, A. R.; Youn, S. W. Eur. J. Org. Chem. 2011, 2011, 3904
33. Jagdale, A. R.; Park, J. H.; Youn, S. W. J. Org. Chem. 2011, 76, 7204
34. Dombray, T.; Blanc, A.; Weibel, J. M.; Pale, P. Org. Lett. 2010, 12, 5362
35. Lin, C.-C.; Teng, T.-M.; Odedra, A.; Liu, R.-S. J. Am. Chem. Soc. 2007, 129, 3798
36. Lin, C.-C.; Teng, T.-M.; Tsai, C.-C.; Liao, H.-Y.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16417
37. Melhado, A. D.; Amarante, G. W.; Wang, Z. J.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 3517
38. González, A. Z.; Toste, F. D. Org. Lett. 2010, 12, 200
39. Alonso, I.; Trillo, B.; López, F.; Montserrat, S.; Ujaque, G.; Castedo, L.; Lledós, A.; Mascareñas, J. L. J. Am. Chem. Soc. 2009, 131, 13020
40. Teller, H.; Flügge, S.; Goddard, R.; Fürstner, A. Angew. Chem., Int. Ed. 2010, 49, 1949
41. Francos, J.; Grande-Carmona, F.; Faustino, H.; Iglesias-Sigüenza, J.; Díez, E.; Alonso, I.; Fernández, R.; Lassaletta, J. M.; López, F.; Mascareñas, J. L. J. Am. Chem. Soc. 2012, 134, 14322
42. Hashmi, A. S. K.; Kurpejović, E.; Wölfle, M.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2007, 349, 1743
43. Lenaršič, R.; Kočevar, M.; Polanc, S. J. Org. Chem. 1999, 64, 2558
44. Suárez-Pantiga, S.; Hernández-Díaz, C.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2012, 51, 1
45. Teller, H.; Flügge, S.; Goddard, R.; Fürstner, A. Angew. Chem., Int. Ed. 2010, 49, 1949
46. Teller, H.; Fürstner, A. Chem.-Eur. J. 2011, 17, 7764
47. González, A. Z.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 5500
48. González, A. Z.; Toste, F. D. Org. Lett. 2010, 12, 200
49. Theoretical Inorganic Chemistry II; Albini, A.; Kisch, H., Eds.; Springer: Berlin, 1976; pp 105-145.
50. The calculations were carried out with the Gaussian 03: Frisch, M. J.; Gaussian03, revisionD.03; Gaussian, Inc.: Wallingford, CT., 2004, (for complete ref 16, see the Supporting Information).
51. Cabello, N.; Jiménez-Núũez, E.; Buñuel, E.; Cárdenas, D. J.; Echavarren, A. M. Eur. J. Org. Chem. 2007, 4217