Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: Efficient access to highly substituted cyclobutanes

Organic Letters

Volumn 16, Issue 23, 2014, Pages 6196-6199

  Bernal Albert, Paloma ^a   Faustino, Hélio ^a   Gimeno, Ana ^c   Asensio, Gregorio ^c   Mascarenas, José L ^a   López, Fernando ^a,b  

^a s n   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOBUTANE DERIVATIVE; GOLD; HYDRAZONE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOADDITION REACTION; CYCLOBUTANES; GOLD; HYDRAZONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84916210114     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503121q     Document Type: Article

References (46)

1. Dembitsky, V. J. Nat. Prod. 2008, 62, 1
2. Hansen, T. V.; Stenstrom, Y. Organic Synthesis: Theory and Applications 2001, 5, 1
3. Namyslo, J. C.; Kaufmann, D. Chem. Rev. 2003, 103, 1485
4. Fu, N.-Y.; Chan, S.-H.; Wong, H. N. C. In The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons: West Sussex, 2005; Vol. 1, Chapter 9.
5. Baldwin, J. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 63.
6. Crimmins, M. T. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol 5, p 123.
7. Lee-Ruff, E. In The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons, Ltd.: West Sussex, 2005; Vol. 1, Chapter 8.
8. Hehn, J. P.; Muller, C.; Bach, T. In Handbook of Synthetic Photochemistry; Wiley-VCH: Weinhem, 2010; p 171.
9. Inanaga, K.; Takasu, K.; Ihara, M. J. Am. Chem. Soc. 2004, 126, 1352
10. Schmidt, A. W.; Knolker, H.-J. Synlett 2010, 2207
11. Brimioulle, R.; Bach, T. Science 2013, 342, 840
12. Parthasarathy, K.; Cheng, C. H. In Comprehensive Organic Synthesis II, 2 nd ed.; Knochel, P.; Molander, G. A., Eds.; Elsevier: Amsterdam, 2014; p 222.
13. Tam, W.; Goodreid, J.; Cockburn, N. Curr. Org. Synth. 2014, 6, 219
14. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Soc. Rev. 2010, 39, 783
15. Gulías, M.; Collado, A.; Trillo, B.; López, F.; Oñate, E.; Esteruelas, M. A.; Mascareñas, J. L. J. Am. Chem. Soc. 2011, 133, 7660
16. Li, X. X.; Zhu, L. L.; Zhou, W.; Chen, Z. L. Org. Lett. 2012, 14, 436
17. Suárez-Pantiga, S.; Hernández-Díaz, C.; Piedrafita, M.; Rubio, E.; González, J. M. Adv. Synth. Catal. 2012, 354, 1651
18. Faustino, H.; Bernal, P.; Castedo, L.; López, F.; Mascareñas, J. L. Adv. Synth. Catal. 2012, 354, 1658
19. Suárez-Pantiga, S.; Hernández-Díaz, C.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2012, 51, 11552
20. Montserrat, S.; Faustino, H.; Lledós, A.; Mascareñas, J. L.; López, F.; Ujaque, G. Chem.-Eur. J. 2013, 19, 15248
21. Lazny, R.; Nodzewska, A. Chem. Rev. 2010, 110, 1386
22. Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259
23. Lomberget, T.; Baragona, F.; Fenet, B.; Barret, R. Org. Lett. 2006, 8, 3919
24. Hashimoto, T.; Omote, M.; Maruoka, K. Angew. Chem., Int. Ed. 2011, 50, 3489
25. Hashimoto, T.; Kimura, H.; Maruoka, K. Angew. Chem., Int. Ed. 2010, 49, 6844
26. Sridharan, V.; Ribelles, P.; Estévez, V.; Villacampa, M.; Ramos, M. T.; Perumal, P. T.; Menéndez, J. C. Chem.-Eur. J. 2012, 18, 5056
27. Kamitori, Y.; Hojo, M.; Msuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519
28. Hegedus, L. S.; Sestrick, M. R.; Michaelson, E. T.; Harrington, P. J. J. Org. Chem. 1989, 54, 4141
29. Brehme, R.; Enders, D.; Fernández, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2007, 5629
30. Crespo-Pelna, A.; Monge, D.; Martín-Zamora, E.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2012, 134, 12912
31. N, N -Dialkyl hydrazones are typically used as ancillary ligands in transition metal catalysis.(8) For isolated examples of their use as reactants, see
32. Ros, A.; López-Rodríguez, R.; Estepa, B.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2012, 134, 4573
33. Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem., Int. Ed. 2013, 52, 5346
34. Prieto, A.; Jeamet, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Org. Lett. 2014, 16, 4770
35. Monge, D.; Martín-Zamora, E.; Vázquez, J.; Alcarazo, M.; álvarez, E.; Fernández, R.; Lassaletta, J. M. Org. Lett. 2007, 9, 2867
36. Faustino, H.; López, F.; Castedo, L.; Mascareñas, J. L. Chem. Sci. 2011, 2, 633
37. Faustino, H.; Alonso, I.; Mascareñas, J. L.; López, F. Angew. Chem., Int. Ed. 2013, 52, 6526
38. Zhou, W.; Li, X. X.; Li, G. H.; Wu, Y.; Chen, Z. Chem. Commun. 2013, 49, 3552
39. Li, G. H.; Zhou, W.; Li, X. X.; Bi, Q. W.; Wang, Z.; Zhao, Z. G.; Hu, W. X.; Chen, Z. Chem. Commun. 2013, 49, 4770
40. Lu, T.; Lu, Z. J.; Ma, Z. X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862
41. For a cycloaddition leading to products related to 5aa, see: Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629
42. Braun, I.; Rudroff, F.; Mihovilovic, M. D.; Bach, T. Angew. Chem., Int. Ed. 2006, 45, 5541 and references therein
43. Lu, P.; Bach, T. Angew. Chem., Int. Ed. 2012, 51, 1261
44. Alibes, R.; álvarez-Larena, A.; de March, P.; Figueredo, M.; Font, J.; Parella, T.; Rustullet, A. Org. Lett. 2006, 8, 491
45. Kimber, M. C. Org. Lett. 2010, 12, 1128
46. Hill, A. W.; Elsegood, M. R.; Kimber, M. C. J. Org. Chem. 2010, 75, 5406