Highly stereoselective facile synthesisl of 2-acetoxy-1,3(E)-alkadienes via a Rh(I)-catalyzed isomerization of 2,3- allenyl carboxylates

Organic Letters

Volumn 13, Issue 8, 2011, Pages 1920-1923

  Zhang, Xiaobing ^a   Fu, Chunling ^a   Ma, Shengming ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955408269     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200198z     Document Type: Article

References (61)

1. For examples, see: (a) Kropf, H.; Schröder, R.; Fölsing, R. Synthesis 1977, 12, 894.
2. Shea, K. J.;Wda, E. J. Am. Chem. Soc. 1982, 104, 5715.
3. Potman, R. P.; Kleef, F. J.; Scheeren, H. W. J. Org. Chem. 1985, 50, 1955.
4. Shea, K. J.; Fruscella, W. M.; Carr, R. C.; Burke, L. D.; Cooper, D. K. J. Am. Chem. Soc. 1987, 109, 447.
5. Hansen, D. W.; Pappo, R.; Garland, R. B. J. Org. Chem. 1988, 53, 4244.
6. Philippot, K.; Devanne, D.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1990, 17, 1199.
7. Stoodley, R. J.; Yuen, W.-H. Chem. Commun. 1997, 15, 1371.
8. Areces, P.; Jiménez, J. L.; Pozo, M. C.; Román, E.; Serrano, J. A. J. Chem. Soc., Perkin Trans. 1 2001, 754.
9. Roversi, E.; Vogel, P. Helv. Chim. Acta 2002, 85, 761.
10. Pollini, G. P.; Bianchi, A.; Casolari, A.; Risi, C.; Zanirato, V.; Bertolasi, V. Tetrahedron: Asymmetry 2004, 15, 3223.
11. Boaz, N. W. Tetrahedron Lett. 1998, 39, 5505.
12. Bennett, G. J.; Lee, H.-H. J. Chem. Soc., Perkin Trans. 1 1986, 633.
13. Seltzer, S. J. Org. Chem. 1995, 60, 1189.
14. Tode, C.; Yamano, Y.; Ito, M. J. Chem. Soc., Perkin Trans. 1 2002, 1581.
15. Werntz, J. H. J. Am. Chem. Soc. 1935, 57, 204.
16. Mitsudo, T.; Hori, Y.; YamakaW, Y.;Wtanabe, Y. J. Org. Chem. 1987, 52, 2230.
17. Kalita, B.; Bezbarua, M. S.; Barua, N. C. Synth. Commun. 2002, 32, 3181.
18. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
19. Zhang, L.;Weng, S. J. Am. Chem. Soc. 2006, 128, 1442.
20. Zhao, J.; Hughes, C. O.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 7436.
21. Weng, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414.
22. Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
23. Lemiere, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207.
24. Yu, M.; Li, G.;Weng, S.; Zhang, L. Adv. Synth. Catal. 2007, 349, 871.
25. Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244.
26. Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Ange W. Chem., Int. Ed. 2008, 47, 718.
27. Davies, P. W.; Albrecht, S. J.-C. Chem. Commun. 2008, 238.
28. Dudnik, A. S.; Schwier, T.; Gevorgyan, V. Org. Lett. 2008, 10, 1465.
29. Mauleón, P.; Krinsky, J. L.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 4513.
30. Pérez, A. G.; López, G. S.; Marco-Contelles, J.; Faza, O. N.; Soriano, E.; Lera, A. R. J. Org. Chem. 2009, 74, 2982.
31. Yu, M.; Zhang, G.; Zhang, L. Tetrahedron 2009, 65, 1846.
32. Dudnik, A. S.; Schwier, T.; Gevorgyan, V. Tetrahedron 2009, 65, 1859.
33. Dudnik, A. S.; Schwier, T.; Gevorgyan, V. J. Orgnometallic. Chem. 2009, 694, 482.
34. Garayalde, D.;Gómez-Bengoa, E.; Huang, X.; Goeke, A.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 4720.
35. Barluenga, J.; Riesgo, L.; Vicente, R.; López, Z. A.; Tomás, M. J. Am. Chem. Soc. 2007, 129, 7772.
36. Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868.
37. ImagaW, H.; Asai, Y.; Takano, H.; Hamagaki, H.; NishizaW, M. Org. Lett. 2006, 8, 447.
38. Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2007, 72, 1443.
39. Ji, K.-G.; Shu, X.-Z.; Chen, J.; Zhao, S.-C.; Zheng, Z.-J.; Lu, L.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2008, 10, 3919.
40. Lu, L.; Liu, X.-Y.; Shu, X.-Z.; Yang, K.; Ji, K.-G.; Liang, Y.-M. J. Org. Chem. 2009, 74, 474.
41. Caruana, P. A.; Frontier, A. J. Tetrahedron 2007, 63, 10646.
42. Bray, C. V.-L.;Dérien, S.; Dixneuf, P. H. Ange W. Chem., Int. Ed. 2009, 48, 1439.
43. Shibata, Y.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 7896.
44. Weng, S.; Zhang, L. Org. Lett. 2006, 8, 4585.
45. Li, G.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740.
46. For examples of stereoselectivivty synthesis of 1,3-alkadienes from allenols, see:
47. Shen, Q.; Hammond, G. B. Org. Lett. 2001, 3, 2213.
48. Horváth, A.; Bäckvall, J.-E. J. Org. Chem. 2001, 66, 8120.
49. Ma, S.;Weng, G. Tetrahedron Lett. 2002, 43, 5723.
50. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C. Eur. J. Org. Chem. 2005, 98.
51. Deng, Y.; Jin, X.; Ma, S. J. Org. Chem. 2007, 72, 5901.
52. Deng, Y.; Yu, Y.; Ma, S. J. Org. Chem. 2008, 73, 585.
53. Alcaide, B.; Almendros, P.; Campo, T. M.; Carrascosa, R. Chem.;Asian J. 2008, 3, 1140.
54. Deng, Y.; Li, J.; Ma, S. Chem.;Eur. J. 2008, 14, 4263.
55. Deng, Y.; Jin, X.; Fu, C.; Ma, S. Org. Lett. 2009, 11, 2169.
56. Durán-Galván, M.; Connell, B. T. Eur. J. Org. Chem. 2010, 2445.
57. Buzas, A. K.; Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 985.
58. Crystal data for E-2k: C21H21NO4,M W=351.39, monoclinic, space group P2(1)/c, final R indices [I > 2σ(I)], R1 = 0.0608,wR2 = 0.1451, R indices (all data) R1=0.0694,wR2=0.1500, a=7.7254(7) Å , b=8.2025(7)Å , c=29.583(3)Å , α=90°, β=96.638(3)o, γ=90°, V=1862(3)Å 3, T=173 K, Z=4, reflections collected/unique: 20256/ 3269 (Rint = 0.0364), number of observations [>2σ(I)] 2783, parameters: 243. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center (CCDC 805894).
59. Bestmann, H.-J.; Hartung, H. Chem. Ber. 1966, 99, 1198.
60. Romo, J.; Rosenkranz, G.; Sondheimer, F. J. Am. Chem. Soc. 1954, 79, 5034.
61. Ma, S.; Gu, Z.; Deng, Y. Chem. Commun. 2006, 94.