Isoindoles and dihydroisoquinolines by gold-catalyzed intramolecular hydroamination of alkynes

Chemical Communications

Volumn 6, Issue 6, 2006, Pages 661-662

  Kadzimirsz, Daniel ^a   Hildebrandt, Dirk ^a   Merz, Klaus ^a   Dyker, Gerald ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMINO ACID; GOLD; ISOINDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROAMINATION; SYNTHESIS;

EID: 33646024927     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b516017k     Document Type: Article

References (53)

1. G. Dyker Angew. Chem. 2000 112 4407
2. G. Dyker Angew. Chem., Int. Ed. 2000 39 4237
3. A. S. K. Hashmi Gold Bull. 2004 37 51
4. A. Hoffmann-Röder N. Krause Org. Biomol. Chem. 2005 3 387
5. A. S. K. Hashmi Angew. Chem., Int. Ed. 2005 54 6990
6. Y. Luo C. J. Li Chem. Commun. 2004 1930
7. Z. Shi C. He J. Am. Chem. Soc. 2004 126 13596
8. S. T. Staben J. J. Kennedy-Smith F. D. Toste Angew. Chem. 2004 116 5464
9. S. T. Staben J. J. Kennedy-Smith F. D. Toste Angew. Chem., Int. Ed. 2004 43 5350
10. X. Yao C.-J. Li J. Am. Chem. Soc. 2004 126 6884
11. A. S. K. Hashmi M. Rudolph J. P. Weyrauch M. Wölfle W. Frey J. W. Bats Angew. Chem. 2005 117 2858
12. A. S. K. Hashmi M. Rudolph J. P. Weyrauch M. Wölfle W. Frey J. W. Bats Angew. Chem., Int. Ed. 2005 44 2798
13. Y. Harrak C. Blaszykowski M. Bernard K. Cariou E. Mainetti V. Mouries A.-L. Dhimane L. Fensterbank M. Malacria J. Am. Chem. Soc. 2004 126 8656
14. C. Nieto-Oberhuber M. P. Muñoz E. Buñuel C. Nevado D. J. Cárdenas A. M. Echavarren Angew. Chem. 2004 116 2456
15. C. Nieto-Oberhuber M. P. Muñoz E. Buñuel C. Nevado D. J. Cárdenas A. M. Echavarren Angew. Chem., Int. Ed. 2004 43 2402
16. M. R. Luzung J. P. Markham F. D. Toste J. Am. Chem. Soc. 2004 126 10858
17. V. Mamane T. Gress H. Krause A. Fürstner J. Am. Chem. Soc. 2004 126 8654
18. K. Miki T. Yokoi F. Nishino Y. Kato Y. Washitake K. Ohe S. Uemura J. Org. Chem. 2004 69 1557
19. T. Yao X. Zhang R. C. Larock J. Am. Chem. Soc. 2004 126 11164
20. S. Antoniotti E. Genin V. Michelet J. P. Genêt J. Am. Chem. Soc. 2005 127 9976
21. N. Asao K. Sato Menggenbateer Y. Yamamoto J. Org. Chem. 2005 70 3682
22. L. Zhang S. A. Kozmin J. Am. Chem. Soc. 2005 127 6962
23. C.-G. Yang C. He J. Am. Chem. Soc. 2005 127 6966
24. J. Zhu N. P. Grigoriadis J. P. Lee J. A. Porco, Jr J. Am. Chem. Soc. 2005 127 9342
25. J. P. Markham S. T. Staben F. D. Toste J. Am. Chem. Soc. 2005 127 9708
26. A. S. K. Hashmi P. Sinha Adv. Synth. Catal. 2004 346 432
27. A. S. K. Hashmi M. Rudolph J. P. Weyrauch M. Wölfle W. Frey J. W. Bats Angew. Chem., Int. Ed. 2005 44 2798
28. G. Dyker D. Hildebrandt J. Liu K. Merz Angew. Chem. 2003 115 4536
29. G. Dyker D. Hildebrandt J. Liu K. Merz Angew. Chem., Int. Ed. 2003 42 4399
30. G. Dyker D. Hildebrandt J. Org. Chem. 2005 70 6093
31. I. Ugi, S. Lohberger, R. Karl, B. M. Trost, I. Fleming and C. H. Heathcock, The Passerini and Ugi reaction, in Comprehensive Organic Chemistry, Vol. 2, Ch. 4.6, pp. 1083-1109, Pergamon Press, Oxford, 1991
32. A. Demharter W. Hörl E. Herdtweck I. Ugi Angew. Chem. 1996 108 185
33. A. Demharter W. Hörl E. Herdtweck I. Ugi Angew. Chem., Int. Ed. 1996 35 173
34. A. Dömling I. Ugi Angew. Chem. 2000 112 3301 3344
35. A. Dömling I. Ugi Angew. Chem., Int. Ed. 2000 39 3168
36. I. Ugi W. Hörl C. Hanusch-Kompa T. Schmid E. Herdtweck Heterocycles 1998 47 965
37. G. Dyker Angew. Chem. 1997 109 1777
38. G. Dyker Angew. Chem., Int. Ed. Engl. 1997 36 1700
39. G. Dyker K. Breitenstein G. Henkel Tetrahedron: Asymmetry 2002 13 1929
40. K. Sonogashira Y. Tohda N. Hagihara Tetrahedron Lett. 1975 50 4467
41. S. Thorand N. Krause J. Org. Chem. 1998 63 8551
42. G. Dyker W. Stirner G. Henkel Eur. J. Org. Chem. 2000 1433
43. T. E. Müller M. Grosche E. Herdtweck A.-K. Pleier E. Walter Y.-K. Yan Organometallics 2000 19 170
44. E. Mizushima T. Hayashi M. Tanaka Org. Lett. 2003 5 3349
45. G. B. Bajracharya Z. Huo Y. Yamamoto J. Org. Chem. 2005 70 4883
46. Y. Luo Z. Li C.-J. Li Org. Lett. 2005 7 2675
47. -1, R1 = 0.0509 for 2835 observed reflections (I > 2σ(I)), wR2 = 0.1214 for all reflections
48. α radiation, λ = 0.71707 Å, T = 203 K). The structure was solved by direct methods and refined by full matrix least squares using SHELXTL-97. All non-hydrogen atoms were refined using anisotropic thermal parameters; hydrogen atoms were included by use of a riding model and fixed isotropic thermal parameters. CCDC 289676. For crystallographic data in CIF or other electronic format see DOI: 10.1039/b516017k
49. P. Sohar F. Miklos A. Csampai G. Stajer J. Chem. Soc., Perkin Trans. 1 2001 5 558
50. R. P. Kreher N. Kohl Angew. Chem. 1984 96 507
51. R. P. Kreher N. Kohl Angew. Chem., Int. Ed. 1984 23 517
52. D. E. Remy F. H. Bissett J. Org. Chem. 1978 43 4469
53. J. Bornstein D. E. Remy J. E. Shields J. Chem. Soc., Chem. Commun. 1972 20 1149