PdII-catalyzed oxidative dimeric cyclization-coupling reaction of 2,3-allenoic acids: an efficient synthesis of bibutenolide derivatives

Chemistry - A European Journal

Volumn 11, Issue 8, 2005, Pages 2351-2356

  Ma, Shengming ^a   Yu, Zhanqian ^a   Gu, Zhenhua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenes; Butenolides; Homogeneous catalysis; Palladium

Indexed keywords

DERIVATIVES; DIMERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IODINE COMPOUNDS; OXIDATION; PALLADIUM; PHENOLS; REACTION KINETICS; SOLUTIONS; SYNTHESIS (CHEMICAL);

AEROBIC OXIDATION; ALLENES; BUTENOLIDES; HOMOGENEOUS CATALYSIS;

CATALYSIS;

EID: 17444416753     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401079     Document Type: Article

References (45)

1. a) Allenes in Organic Synthesis (Eds.: H. F. Schuster, G. M. Coppola), Wiley, New York, 1984, pp. 1-8;
2. b) The Chemistry of Ketenes, Allenes, and Related Compounds, Part 1 (Ed.: S. Patai), Wiley, New York, 1980, pp. 1-154.
3. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
4. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
5. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
6. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
7. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
8. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
9. For some typical examples of axial chirality transfer, see: a) G. Kresze, L. Kloimstein, W. Runge, Justus Liebigs Ann. Chem. 1976, 64, 979; b) S. Musierowicz, A. E. Wroblewski, Tetrahedron 1978, 34, 461; c) J. A. Marshall, W. A. Wolf, E. M. Wallace, J. Org. Chem. 1997, 62, 367; d) S. Ma, S. Wu, Chem. Commun. 2001, 441; e) S. Ma. Z. Shi, Chem. Commun. 2002, 540; f) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943; g) S. Ma, Z. Yu, J. Org. Chem. 2003, 68, 6149.
10. For most recent results of the synthesis of butenolides from this group, see: a) S. Ma, Z. Shi, S. Wu, Tetrahedron: Asymmetry 2001, 12, 193; b) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239; c) S. Ma, Z. Yu, Angew. Chem. 2003, 115, 1999; Angew. Chem. Int. Ed. 2003, 42, 1955; d) For an account, see: S. Ma, Acc. Chem. Res. 2003, 36, 701.
11. For most recent results of the synthesis of butenolides from this group, see: a) S. Ma, Z. Shi, S. Wu, Tetrahedron: Asymmetry 2001, 12, 193; b) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239; c) S. Ma, Z. Yu, Angew. Chem. 2003, 115, 1999; Angew. Chem. Int. Ed. 2003, 42, 1955; d) For an account, see: S. Ma, Acc. Chem. Res. 2003, 36, 701.
12. For most recent results of the synthesis of butenolides from this group, see: a) S. Ma, Z. Shi, S. Wu, Tetrahedron: Asymmetry 2001, 12, 193; b) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239; c) S. Ma, Z. Yu, Angew. Chem. 2003, 115, 1999; Angew. Chem. Int. Ed. 2003, 42, 1955; d) For an account, see: S. Ma, Acc. Chem. Res. 2003, 36, 701.
13. For most recent results of the synthesis of butenolides from this group, see: a) S. Ma, Z. Shi, S. Wu, Tetrahedron: Asymmetry 2001, 12, 193; b) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239; c) S. Ma, Z. Yu, Angew. Chem. 2003, 115, 1999; Angew. Chem. Int. Ed. 2003, 42, 1955; d) For an account, see: S. Ma, Acc. Chem. Res. 2003, 36, 701.
14. For most recent results of the synthesis of butenolides from this group, see: a) S. Ma, Z. Shi, S. Wu, Tetrahedron: Asymmetry 2001, 12, 193; b) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239; c) S. Ma, Z. Yu, Angew. Chem. 2003, 115, 1999; Angew. Chem. Int. Ed. 2003, 42, 1955; d) For an account, see: S. Ma, Acc. Chem. Res. 2003, 36, 701.
15. For most recent coupling cyclization reaction of other functionalized allenes, see: a) S. Ma, W. Gao, Synlett 2002, 65; b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837; c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104; d) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575; e) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
16. For most recent coupling cyclization reaction of other functionalized allenes, see: a) S. Ma, W. Gao, Synlett 2002, 65; b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837; c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104; d) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575; e) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
17. For most recent coupling cyclization reaction of other functionalized allenes, see: a) S. Ma, W. Gao, Synlett 2002, 65; b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837; c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104; d) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575; e) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
18. For most recent coupling cyclization reaction of other functionalized allenes, see: a) S. Ma, W. Gao, Synlett 2002, 65; b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837; c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104; d) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575; e) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
19. For most recent coupling cyclization reaction of other functionalized allenes, see: a) S. Ma, W. Gao, Synlett 2002, 65; b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837; c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104; d) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575; e) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989.
20. For the recent Pd-catalyzed reaction of allenic amides, see: a) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, T. Ibuka, J. Org. Chem. 2001, 66, 4904; b) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511; c) W.F.J. Karstens, D. Klomp, F.P.J.T. Rutjes, H. Hiemstra, Tetrahedron 2001, 57, 5123.
21. For the recent Pd-catalyzed reaction of allenic amides, see: a) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, T. Ibuka, J. Org. Chem. 2001, 66, 4904; b) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511; c) W.F.J. Karstens, D. Klomp, F.P.J.T. Rutjes, H. Hiemstra, Tetrahedron 2001, 57, 5123.
22. For the recent Pd-catalyzed reaction of allenic amides, see: a) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, T. Ibuka, J. Org. Chem. 2001, 66, 4904; b) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511; c) W.F.J. Karstens, D. Klomp, F.P.J.T. Rutjes, H. Hiemstra, Tetrahedron 2001, 57, 5123.
23. For Pd-catalyzed reaction of 2-(allenyl)malonates, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, Y. Yamamoto, J. Org. Chem. 1999, 64, 694; c) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 55, 2881.
24. For Pd-catalyzed reaction of 2-(allenyl)malonates, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, Y. Yamamoto, J. Org. Chem. 1999, 64, 694; c) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 55, 2881.
25. For Pd-catalyzed reaction of 2-(allenyl)malonates, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, Y. Yamamoto, J. Org. Chem. 1999, 64, 694; c) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 55, 2881.
26. For a review on the palladium-catalyzed chemistry of allenes, see: a) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; b) S. Ma, Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002, p. 1491.
27. For a review on the palladium-catalyzed chemistry of allenes, see: a) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; b) S. Ma, Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002, p. 1491.
28. a) For dimerization of 1,2-allenyl ketones, see: A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382; Angew. Chem. Int. Ed. 2000, 39, 2285;
29. a) For dimerization of 1,2-allenyl ketones, see: A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382; Angew. Chem. Int. Ed. 2000, 39, 2285;
30. b) For a recent highlight, see: A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737; Angew. Chem. Int. Ed. 2000, 39, 3590.
31. b) For a recent highlight, see: A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737; Angew. Chem. Int. Ed. 2000, 39, 3590.
32. S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew. Chem. Int. Ed. 2002, 41, 1775.
33. S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew. Chem. Int. Ed. 2002, 41, 1775.
34. Palladium Reagents and Catalysts: New Perspectives for 21st Century (Ed.: J. Tsuji), Wiley, Chichester (UK), 2004, pp. 27-103.
35. S. Ma, Z. Yu. Org. Lett. 2003, 5, 1507; Corrigendum: S. Ma, Z. Yu. Org. Lett. 2003, 5, 2581.
36. S. Ma, Z. Yu. Org. Lett. 2003, 5, 1507; Corrigendum: S. Ma, Z. Yu. Org. Lett. 2003, 5, 2581.
37. a) Y. Chia, F. Chang, Y. Wu, Tetrahedron Lett. 1999, 40, 7513;
38. b) S. Takahashi, K. Maeda, S. Hirota, T. Nakata, Org. Lett. 1999, 1, 2025;
39. R. C. Larock, B. Riefling, C. A. Fellows, J. Org. Chem. 1978, 43, 131, and references therein.
40. a) J. E. Bäckvall, P. G. Andersson, J. Am. Chem. Soc. 1992, 774, 6374;
41. b) P. G. Andersson, J. E. Bäckvall, J. Org. Chem. 1991, 56, 5349.
42. int =0.1985), restraints: 7, parameters: 300. CCDC 244017 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
43. int=0.0719), no observation [I > 2α(1)] 3086, parameters 300. CCDC 223809 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
44. For the reports on the synthesis of bibutenolide see: a) A. Padwa, F. R. Kinder, J. Org. Chem. 1993, 58, 21; b) F. R. Kinder, A. Padwa, Tetrahedron Lett. 1990, 31, 6835.
45. For the reports on the synthesis of bibutenolide see: a) A. Padwa, F. R. Kinder, J. Org. Chem. 1993, 58, 21; b) F. R. Kinder, A. Padwa, Tetrahedron Lett. 1990, 31, 6835.