Gold-catalyzed tandem cyclizations of 1,6-diynes triggered by internal N- and O-nucleophiles

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4542-4553

  Sperger, Christian A ^a   Fiksdahl, Anne ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC PRODUCTS; CATALYTIC SYSTEM; CYCLIZATIONS; REACTION CONDITIONS; REGIOISOMERS; TANDEM CYCLIZATION;

AMIDES; CARBOXYLIC ACIDS; NUCLEOPHILES; ORGANIC ACIDS; SUBSTRATES; SULFUR COMPOUNDS;

CYCLIZATION;

2 (BUT 2 YNYL) 2 PHENYLHEX 4 YN 1 AMINE; 2 ETHYL 6 ETHYLIDENE 4 PHENYL 1 AZABICYCLO[2.2.1]HEPTANE; 3 (BUT 2 YNYL) 5 ETHYL 3 PHENYL 3,4 DIHYDRO 2H PYRROLE; 4 (BUT 2 YNYL) 2 ETHYL PHENYLPYRROLIDINE; ALKYNE DERIVATIVE; AMIDE; AMINE; CARBOXYLIC ACID; DIMETHYL 2 (BUT 2 YNYL) 2 [3 [2 (ETHYLCARBAMOYL)PHENYL]PROP 2 YNYL] MALONATE; DIMETHYL 2 (BUT 2 YNYL) 2 [3 [2 [(4 METHYLPHENYLSULFONAMIDO)METHYL] PHENYL] PROP 2 YNYL] MALONATE; ETHYL 2 METHYL 5 PHENYL 1 AZABICYCLO[3.2.1]OCT 2 ENE; GOLD; MALONIC ACID DERIVATIVE; METHYL 2 (BUT 2 YNYL) 2 (ETHYLCARBAMOYL)HEX 4 YNOATE; METHYL 2 (BUT 2 YNYL) 2 CARBAMOYLHEX 4 YNOATE; METHYL 3 (BUT 2 YNYL) 5 ETHYLIDENE 2 OXOTETRAHYDRO 3 CARBOXYLATE; METHYL 3 ETHYL 6 ETHYLIDENE 4 METHYLENE 2 OXO 3 AZABICYCLO[3.2.1]OCTANE 1 CARBOXYLATE; METHYL 3 ETHYL 6 METHYL 4 METHYLENE 2 OXO 3 AZABICYCLO[3.3.1]NON 6 ENE 1 CARBOXYLATE; N (2 BROMOBENZYL) 4 METHYLBENZENESULFONAMIDE; N [2 (BUT 2 YNYL) 2 PHENYLHEX 4 YNYL] 4 METHYLBENZENESULFONAMIDE; NITROGEN; NUCLEOPHILE; OXYGEN; PYRROLE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENZYME SUBSTRATE; STEREOCHEMISTRY;

EID: 77954133068     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100712d     Document Type: Article

References (36)

1. Skouta, R.; Li, C. J. Tetrahedron 2008, 64, 4917
2. Shen, H. C. Tetrahedron 2008, 64, 7847
3. Stephen, A.; Hashmi, K. Chem. Rev. 2007, 107, 3180
4. Arcadi, A. Chem. Rev. 2008, 108, 3266
5. Sohel, S. M. A.; Liu, R. S. Chem. Soc. Rev. 2009, 38, 2269
6. Fuerstner, A. Chem. Soc. Rev. 2009, 38, 3208
7. Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. - Eur. J. 2006, 12, 1677
8. Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271
9. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804
10. Ferrer, C.; Amijs, C. H. M.; Echavarren, A. M. Chem. - Eur. J. 2007, 13, 1358
11. Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160
12. Binder, J. T.; Crone, B.; Haug, T. T.; Menz, H.; Kirsch, S. F. Org. Lett. 2008, 10, 1025
13. Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genêt, J. P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112
14. Harkat, H.; Dembelé, A. Y.; Weibel, J. M.; Blanc, A.; Pale, P. Tetrahedron 2009, 65, 1871
15. Harkat, H.; Weibel, J. M.; Pale, P. Tetrahedron Lett. 2006, 47, 6273
16. Robles-Machim, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023
17. Verniest, G.; England, D.; De Kimpe, N.; Padwa, A. Tetrahedron 2010, 66, 1496
18. Verniest, G.; Padwa, A. Org. Lett. 2008, 10, 4379
19. Surmont, R.; Verniest, G.; De Kimpe, N. Org. Lett. 2009, 11, 2920
20. Liu, Y.; Xu, W.; Wang, X. Org. Lett. 2010, 12, 1448
21. Sperger, C.; Fiksdahl, A. Org. Lett. 2009, 11, 2449
22. Genin, E.; Toullec, P. Y.; Marie, P.; Antoniotti, S.; Brancour, C.; Genêt, J. P.; Michelet, V. ARKIVOK 2007, 5, 67
23. Aelterman, W.; De Kimpe, N.; Tyvorskii, V.; Kulinkovich, O. J. Org. Chem. 2001, 66, 53
24. Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391
25. Teles, J. H.; Brode, S.; Chababas, M. Angew. Chem., Int. Ed. 1998, 37, 1415
26. Chan, D. M. T.; Marder, T. B.; Milstein, D.; Taylor, N. J. J. Am. Chem. Soc. 1987, 109, 6385
27. Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066
28. Harrison, T. J.; Dake, G. R. Org. Lett. 2004, 6, 5023
29. Harrison, T. J.; Patrick, O. B.; Dake, G. R. Org. Lett. 2007, 9, 367
30. Guannan, L.; Yu, Z.; Deju, Y.; Dengyou, Z.; Xiao, D.; Hualiang, J.; Hong, L. Adv. Synth. Catal. 2009, 351, 2605
31. Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. - Eur. J. 2006, 12, 1677
32. Sperger, C.; Fiksdahl, A. Org. Lett. 2009, 11, 2449
33. Genin, E.; Toullec, P. Y.; Marie, P.; Antoniotti, S.; Brancour, C.; Genêt, J. P.; Michelet, V. ARKIVOK 2007, 5, 67
34. Liu, C.; Widenhoefer, R. A. Organometallics 2002, 21, 5666
35. Gao, F.; Deng, M.; Qian, C. Tetrahedron 2005, 61, 12238
36. Beak, P.; Musick, T. J.; Chen, C. J. Am. Chem. Soc. 1988, 110, 3538