Gold(I) - Catalyzed domino reaction of aziridinyl alkynes

Chemistry - A European Journal

Volumn 16, Issue 26, 2010, Pages 7725-7729

  Zhang, Zhen ^a   Shi, Min ^a,b  

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

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aziridinyl alkynes; Benzylic cations; Dihydroisoquinolines; Domino reactions; Gold; Tetrahydroisoquinolines

Indexed keywords

BENZYLIC CATION; CHEMICAL EQUATIONS; CONTROL EXPERIMENTS; DIASTEREOSELECTIVITIES; DIHYDROISOQUINOLINES; DOMINO REACTIONS; PLAUSIBLE MECHANISMS; STERICALLY CONGESTED; STRUCTURAL MOTIFS; TETRAHYDROISOQUINOLINES;

ACETYLENE; DEUTERIUM; GOLD COMPOUNDS; POSITIVE IONS; REACTION KINETICS;

GOLD;

EID: 77954338179     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000628     Document Type: Article

References (43)

1. For selected recent reviews on gold-catalyzed reactions, see: a) A. S. K. Hashmi, Chem. Rev. 2007, 107. 3180-3211;
2. b) N. Bongers, N. Krause, Angew. Chem. 2008, 120, 2208-2211;
3. Angew. Chem. Int. Ed. 2008, 47. 2178-2181;
4. c) H. C. Shen. Tetrahedron 2008, 64. 3885-3903;
5. d) H. C. Shen. Tetrahedron 2008, 64. 7847-7870;
6. e) J. Muzart, Tetrahedron 2008, 64. 5815-5849;
7. f) R. Skouta. C.-J. Li. Tetrahedron 2008, 64. 4917-4938;
8. g) Z. Li, C. Brouwer. C. He. Chem. Rev. 2008, 108. 3239-3265;
9. h) A. Arcadi. Chem. Rev. 2008, 108. 3266-3325;
10. i) E. Jiménez-Núñez, A.M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
11. j) D. J. Oorin, B. D. Sherry. F. D. Toste. Chem. Rev. 2008, 108, 3351-3378;
12. k) N. T. Patil. Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442;
13. l) S. F. Kirsch. Synthesis 2008, 3183-3204.
14. R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc. Perkin Trans. 1 1976, 1983-1987.
15. a) A. Padwa. W. H. Pearson. B. W. Lian. S. C. Bergmeier, in: Comprehensive Heterocyclic Chemistry II, Vol 1 (Eds.: A. R. Katritzky, C.W. Rees, E. F. V. Scriven), Pergamon, New York, 1996;
16. b) A. Padwa, A. D. Woolhouse in Comprehensive Heterocyclic Chemistry, Vol. 7 (Ed.: W. Lwowski), Pergamon, Oxford, 1984;
17. c) T. Ibuka, Chem. Soc. Rev. 1998, 27, 145-154.
18. X. Sun. W. W. Sun, R. Fan, J. Wu, Adv. Synth. Catal. 2007, 349, 2151-2155.
19. For the synthesis of substituted isoquinolines through the iodinemediated or gold-catalyzed cyclization of 2-alkynyl benzyl azides or imines; a) N. Asao, S. Yudha. T. Nogami, Y. Yamamoto, Angew. Chem. 2005, 117, 5662-5664;
20. Angew. Chem. Int. Ed. 2005, 44, 5526-5528;
21. b) M. Ohtaka. H. Nakamura. Y. Yamamoto, Tetrahedron Lett. 2004, 45, 7339-7341;
22. c) N. Asao, K. Iso. S. Yudha, Org. Lett. 2006, 8,4149-4151;
23. d) Z. Huo. Y. Yamamoto, Tetrahedron Lett. 2009, 50, 3651-3653;
24. e) D. Fischer, H. Tomeba. N. K. Pahadi, N.T. Patil, Y. Yamamoto. Angew. Chem. 2007, 119, 4848-4850;
25. Angew. Chem. Int. Ed. 2007, 46, 4764-4766;
26. f) D. Fischer, H. Tomeba, N. K. Pahadi. N. T. Patil, Z. Huo. Y. Yamamoto, J. Am. Chem. Soc. 2008, 130, 15720-15725.
27. a) J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730;
28. b) C. M. Tarby. Bioorg. Med. Chem. Lett. 2006, 16, 2095-2100;
29. c) R. Razet, U. Thomet, R. Furtmüller, A. Chiaroni, E. Sigel. W. Sieghart, R. H. Dodd. J. Med. Chem. 2000, 43, 4363-4366.
30. The major isomer has been identified as the syn-configuration on the basis of the NMR spectra and the X-ray crystal structure of 4t (see the Supporting Information).
31. a) C. J. Bungard, J. C. Morris. Org. Lett. 2002, 4, 631-633;
32. b) A. Bermejo. I. Andreu. F. Suvire, S. Léonce. D. H. Caignard, P. Renard. A. Pierre. R. D. Enriz. D. Cortes, N. Cabedo. J. Med. Chem. 2002, 45, 5058-5068:
33. c) P. Iturriaga-Vásquez. R. Miquel, M. D. Ivorra. M. P. D'Ocon. B. K. Casseis, J. Nat. Prod. 2003, 66, 954-957.
34. For aryl-gold(III) species, see; a) Z. Shi. C. He, J. Org. Chem. 2004, 69, 3669-3671;
35. b) Z. Shi. C. He. J. Am. Chem. Soc. 2004, 126, 5964-5965.
36. 4 before it was used.
37. For Friedel-Crafts reactions involving a benzylic cation, see: a) F. Mühlthau. D. Stadler, A. Goeppert. G. A. Olah, G. K. S. Prakash, T. Bach. J. Am. Chem. Soc. 2006, 128, 9668-9675;
38. b) F. Mühlthau. O. Schuster. T. Bach, J. Am. Chem. Soc. 2005, 127, 9348-9349;
39. c) J. Y. L. Chung, D. Mancheno, P. G. Dormer, N. Variankaval. R. G. Ball. N. N. Tsou. Org. Lett. 2008, 10, 4149-4151.
40. a) P. A. Wender, D. Strand, J. Am. Chem. Soc. 2009, 131, 7528-7529;
41. b) P. Dauban. G. Malik, Angew. Chem. 2009, 121, 9188-9191;
42. Angew. Chem. Int. Ed. 2009, 48, 9026-9029.
43. 2-Alkynylaryl epoxide does not give similar results with gold(1) catalysts due to the fact that the generation of zwitterionic intermediates is impossible in this case. For the gold-catalyzed cyclization of 2-alkynylaryl epoxides, see: A. S. K. Hashmi, M. Bührle. R. Salathé. J. W. Bats. Adv. Synth. Catal. 2008, 350, 2059-2064.