Rh(I)-catalyzed mild intramolecular [4+2] cycloaddition reactions of ester-tethered diene-yne compounds

Tetrahedron Letters

Volumn 47, Issue 6, 2006, Pages 891-895

  Saito, Akio ^a   Ono, Takamitsu ^a   Takahashi, Arata ^b   Taguchi, Takeo ^b   Hanzawa, Yuji ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Cycloaddition; Ester tethered diene yne; Rhodium catalyst

Indexed keywords

2 PROPYNYL PENTA 2,4 DIENOATE; 2,4 PENTADIENYL PROPIOLATE; ALCOHOL; ALKADIENE; CATION; ESTER; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; FLUORINATION;

EID: 30344437974     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.155     Document Type: Article

References (55)

1. A.G. Fallis Acc. Chem. Res. 32 1999 464 474
2. Y. Suzuki, T. Murata, K. Takao, and K. Tadano Synth. Org. Chem. Jpn. 60 2002 679 689
3. S. Chackalamannil, R.J. Davies, Y. Wang, T. Asberom, D. Doller, J. Wong, and D. Leon J. Org. Chem. 64 1999 1932
4. J. Jauch Angew. Chem., Int. Ed. 39 2000 2764
5. A. Padwa, M.A. Brodney, M. Dimitroff, B. Liu, and T. Wu J. Org. Chem. 66 2001 3119
6. Y. Suzuki, A. Ohara, K. Sugaya, K. Takao, and K. Tadano Tetrahedron 57 2001 7291
7. L.S.-M. Wong, and M.S. Sherburn Org. Lett. 5 2003 3603
8. M. Inoue, T. Sato, and M. Hirama J. Am. Chem. Soc. 125 2003 10772
9. Reviews on intramolecular Diels-Alder reaction: E. Ciganek W.G. Dauben Organic Reactions Vol. 32 1984 John Wiley & Sons New York 1 374
10. D. Craig Chem. Soc. Rev. 16 1987 187
11. W.R. Roush D.P. Curran Advances in Cycliaddition Vol. 2 1990 JAI Press Greenwich, CT 91 146
12. W.R. Roush B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Press Oxford, UK 513 550
13. The recent examples on IMDA reactions of 3,5-hexadienyl acrylate derivatives, see: M.E. Jung, A. Huang, and T.W. Johnson Org. Lett. 2 2000 1835
14. P. Kim, M. Nantz, M.J. Kurth, and M.M. Olmsteas Org. Lett. 2 2000 1831
15. G.A. Jones, M.N. Paddon-Row, M.S. Sherburn, and C.I. Turner Org. Lett. 4 2002 3789
16. The recent examples on IMDA reactions of 2,4-pentadienyl acrylate derivatives, see: C.I. Turner, L.S.-M. Wong, P. Turner, M.N. Paddon-Row, and M.S. Sherburn Chem. Eur. J. 8 2002 739
17. C.I. Turner, M.N. Paddon-Row, D. Moran, A.D. Payne, M.S. Sherburn, and P. Turner J. Org. Chem. 70 2005 5561
18. 2-Propenyl sorbate gave the IMDA product under hursh conditions (250°C, 120 h). 3-Butenyl sorbate derivatives failed to give cyclized products even at 275°C, see: S.F. Martin, S.A. Williamson, R.P. Gist, and K.M. Smith J. Org. Chem. 48 1983 5170
19. M. Toyota, Y. Wada, and K. Fukumoto Heterocycles 35 1993 111 114
20. D. Cain, D.M. Pawar, M. Stewart, H. Billings Jr., and E.A. Noe J. Org. Chem. 66 2001 6092
21. Review on the conformation and stereoelectronic effect of ester compounds, see: P. Deslongchamps Stereoelectric Effects in Organic Chemistry 1983 Pergamon Press Oxford 54 100
22. A. Saito, H. Ito, and T. Taguchi Org. Lett. 4 2002 4619
23. A. Saito, H. Yanai, and T. Taguchi Tetrahedron 60 2004 12239
24. A. Saito, H. Yanai, and T. Taguchi Tetrahedron Lett. 45 2004 9439
25. Reviews on transition metal catalyzed cyclization: B.M. Trost Acc. Chem. Res. 23 1990 34
26. I. Ojima, M. Tzamarioudaki, Z. Li, and R.J. Donovan Chem. Rev. 96 1996 635
27. B.M. Trost, and M.J. Krische Synlett 1998 1
28. B.M. Trost Chem. Rev. 101 2001 2067
29. C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
30. A. Lei, M. He, and X. Zhang J. Am. Chem. Soc. 124 2002 8198
31. X. Tong, Z. Zhang, and X. Zhang J. Am. Chem. Soc. 125 2003 6370
32. M. He, A. Lei, and X. Zhang Tetrahedron Lett. 46 2005 1823
33. S. Ma, and X. Lu J. Org. Chem. 56 1991 5120
34. Q. Zhang, and X. Lu J. Am. Chem. Soc. 122 2000 7604
35. C. Jia, D. Piao, T. Kitamura, and Y. Fujiwara J. Org. Chem. 65 2000 7516
36. R.S. Jolly, G. Luedtke, D. Sheehan, and T. Livinghouse J. Am. Chem. Soc. 112 1990 4965
37. P.A. Wender, T.E. Jenkins, and S. Suzuki J. Am. Chem. Soc. 117 1995 1843
38. S.R. Gilbertson, G. Hoge, and D.G. Genov J. Org. Chem. 63 1998 1007
39. D.J.R. O'Mahony, D.B. Belanger, and T. Livinghouse Synlett 1998 443
40. D. Motoda, H. Kinoshita, H. Shinokubo, and K. Oshima Angew. Chem., Int. Ed. 43 2004 1860
41. Ni-Catalyzed intramolecular [4+2] cycloaddition reaction of ω-alkynyl dienes, see: P.A. Wender, and T.E. Jenkins J. Am. Chem. Soc. 111 1989 6432
42. To our knowledge, no examples of 2-propynyl penta-2,4-dienoate derivatives have been reported. On the attempted thermal reactions of 2- or 3-alcoxycarbonyl-2-propenyl penta-2,4-dienoates, see: R.K. Boeckman Jr., and D.M. Demko J. Org. Chem. 47 1982 1789
43. J. Mulzer, H. Bock, W. Eck, J. Buschmann, and P. Luger Angew. Chem., Int. Ed. Engl. 30 1991 414
44. J. Ishihara, J. Miyakawa, T. Tsujimoto, and A. Murai Synlett 12 1997 1417
45. Thermal reactions of 2,4-pentadienyl propiolates, see: J.D. White, and B.G. Sheldon J. Org. Chem. 46 1981 2273
46. D.H. Birtwhistle, J.M. Brown, and M.W. Foxton Tetrahedron 44 1998 7309
47. C.I. Turner, R.M. Williamson, M.N. Paddon-Row, and M.S. Sherburn J. Org. Chem. 66 2001 3963
48. R.F. Pradilla, R. Baile, and S. Tortosa Chem. Commun. 2003 2476
49. 2/LiCl-Catalyzed reaction of 2,4-pentadienyl propiolate derivatives has been reported to give intramolecular carbochlorination products, see: Y.I.M. Nilsson, R.G.P. Gatti, P.G. Andersson, and J.E. Backvall Tetrahedron 52 1996 7511
50. 2O.
51. Neither THF nor acetone were effective sovents for the cyclization. The reason for the difference in the efficiency of the fluorinated alcohols and the other polar solvents is unclear.
52. 2O or DMSO is highly efficient in intramolecular cyclizations of ester compounds. M.E. Jung Synlett 1999 843
53. H. Yorimitsu, H. Shinokubo, and K. Oshima Synlett 2002 674
54. H. Yanai, A. Saito, and T. Taguchi Tetrahedron 61 2005 7987
55. Rhodium chloride complex such as Willkinson's catalyst accelerates the [4+2] cycloadditon of 1,3-diene-8-yne or 1,3,8-triene derivatives in TFE. It has been suggested that TFE enhances the polarizability of the Rh-Cl bond. See, Refs. 13a and 13d.