Phosphine-free Palladium-catalyzed allene carbopalladation/allylie alkylation domino sequence: A new route to 4-(α-Styryl) γ-lactams

Chemistry - A European Journal

Volumn 15, Issue 17, 2009, Pages 4224-4227

  Kammerer, Claire ^a   Prestat, Guillaume ^a   Madec, David ^a   Poli, Giovanni ^a  

^a Université Pierre et Marie Curie   (France)

Author keywords

Allenes; Domino reactions; Lactams; Nitrogen helorocyclcs; Palladium

Indexed keywords

ALLENES; ALLENYL; ALLYL SPECIES; AZA ANALOGUES; DIASTEREOISOMER; DOMINO REACTIONS; DOUBLE BONDS; ELECTRON-WITHDRAWING SUBSTITUENTS; ENOLATE; FUNCTIONALIZATION; HETEROCYCLE SYNTHESIS; HEXAMETHYL PHOSPHORAMIDE; LACTAMS; MALONAMIDE; MODEL COUPLINGS; PALLADATION; PHOSPHINE-FREE; STEREO-SELECTIVE;

ALKYLATION; AMIDES; HYDROCARBONS; PALLADIUM; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SODIUM;

COORDINATION REACTIONS;

EID: 65449184593     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900184     Document Type: Article

References (69)

1. a) Modem Allene Chemistry, Vol.2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim. 2004;
2. b) S. Ma in Topics in Organ-ometallic Chemistry, Vol. 14 (Ed.: J. Tsuji), Springer, Berlin, Heidelberg. 2005, pp. 183-210;
3. c) S. Ma, Chem, Rev. 2005, 105, 2829-2871;
4. d) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem, Rev. 2000, 100, 3067-3125.
5. For recent reviews, see: a) R. W. Bates. V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12-21;
6. b) G. Zeni, R. C. Larock, Chem, Rev. 2006, 106, 4644-4680;
7. c) G. Balme, E. Bossharth, N. Monleiro, Eur. J. Org. Chem. 2003, 4101-4111;
8. d) S. Ma, Acc. Chem, Res. 2003, 36, 701-712;
9. e) H. Ohno, Chem. Pharm. Bull. 2005, 53, 1211-1226.
10. a) R. R. Stevens, G. G. Shier, J. Organomet. Chem. 1970, 21, 495-499;
11. b) T. Bai, L. Xue, P. Xue, J. Zhu, H. H.-Y. Sung, S. Ma, I. D. Williams, Z. Lin, G. Jia, Organometallics 2008, 27, 2614-2626. For two pioneering examples of catalytic experiments, see:
12. c) I. Shimizu, J. Tsuji. Chem. Lett. 1984, 233-236;
13. d) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1984, 25, 4505-4508.
14. For leading references, see: a) M. Ahmar, B. Cazes, J. Gore, Tetrahedron 1987, 43, 3453-3463;
15. b) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847;
16. c) S. Ma, N. Jiao, Q. Yang, Z. Zheng, J. Org. Chem. 2004, 69, 6463-6466;
17. d) C. H. Oh, C. Y. Rhim, C. H. Song, J. H. Ryu, Chem. Lett. 2002, 31, 1140-1141.
18. For leading references, see: a) S. Ma, Z. Shi. J. Org. Chem, 1998, 63, 6387-6389;
19. b) S. Ma. S. Zhao, J. Am. Chem. Soc. 1999, 121, 7943-7944;
20. c) S. Ma, J. Zhang, L. Lu, Chem. Eur J. 2003, 9, 2447-2456;
21. d) S. Ma. Z. Zheng. X. Jiang, Org. Lett. 2007, 9, 529-531;
22. e) S. Ma. H. Xie, J. Org. Chem. 2002, 67, 6575-6578;
23. f) S. Ma, F. Yu, J. Li, W. Gao, Chem. Eur J. 2007, 13, 247-254;
24. g) Q. Yang, X. Jiang, S. Ma. Chem, Eur. J. 2007, 13, 9310-9316;
25. h) X. Cheng, S. Ma. Angew. Chem. 2008, 120, 4657-4659;
26. Angew. Chem. Int. Ed. 2008, 47, 4581-4583;
27. i) W. Shu, Q. Yang, G. Jia, S. Ma, Tetrahedron 2008, 64, 11159-11166;
28. j) H. Ohno, M. Anzai, A. Toda, S. Ohishi, N. Fujii, T. Tanaka, Y. Takemoto, T. Ibuka, J. Org. Chem. 2001, 66, 4904-4914;
29. k) F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens. H. E. Schoemaker. H. Hiemstra, Org. Lett. 1999, 1, 717-720;
30. 1) K. Hiroi. Y. Hiratsuka, K. Watanabe, I. Abe, F. Kato. M. Hiroi, Tetrahedron: Asymmetry 2002, 13, 1351-1353;
31. m) G. R. Cook, W. Xu. Heterocycles 2006, 67, 215-232.
32. a) R. Grigg, I. Köppen, M. Rasparini, V. Sridharan, Chem. Commun. 2001, 964-965;
33. b) A. Okano, T. Mizutani, S. Oishi, T. Tanaka, H. Ohno, N. Fujii, Chem. Commun. 2008, 3534-3536.
34. a) G. Poli, G. Giambastiani, J. Org. Chem. 2002, 67, 9456-9459;
35. b) S. Lemaire, G. Prestat, G. Giambastiani, D. Madec, B. Pacini, G. Poli, J. Organomet. Chem. 2003, 687, 291-300;
36. c) G. Maitro, S. Vogel, G. Prestat, D. Madec, G. Poli, Org. Lett. 2006, 8, 5951-5954;
37. d) C. Kammerer, G. Prestat, T. Gaillard, D. Madec, G. Poli, Org. Lett. 2008, 10, 405-408;
38. e) E Mingoia, M. Vitale, D. Madec, G. Pre-stat, G. Poli, Tetrahedron Lett. 2008, 49, 760-763.
39. a) G. Giambastiani, B. Pacini, M. Porcelloni, G. Poli, J. Org. Chem. 1998, 65, 804-805;
40. b) P.-O. Norrby, M. M. Mader, M. Vitale, G. Pre-stat, G. Poli, Organometallics 2003, 22, 1849-1855;
41. c) S. Lemaire, G. Giambastiani, G. Prestat, G. Poli, Eur. J. Org. Chem. 2004, 2840-2847;
42. d) D. Madec, G. Prestat, E. Martini, P. Fristrup, G. Poli, P.-O. Norrby, Org. Lett. 2005, 7, 995-998;
43. e) G. Maitro, G. Prestat, D. Madec, G. Poli, Synlett 2006, 1055-1058;
44. f) M. Bui The Thuong, S. Sottocornola, G. Prestat, G. Broggini, D. Madec, G. Poli, Synlett 2007, 1521-1524.
45. As opposed to a pseudo-domino process: a) G. Prestat, G. Poli, Chemtracts: Org. Chem. 2004, 17, 97-103;
46. b) Ref. 7.
47. S. Ma, S. Zhao, Org. Lett. 2000, 2, 2495-2497.
48. a) M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133-5209;
49. b) J. C. Bayon, C. Claver, A. M. Masdeu-Bultó, Coord. Chem. Rev. 1999, 193-195, 73-145;
50. c) D. Madec, F. Mingoia, C. Macovei, G. Maitro, G. Giambastiani, G. Poli, Eur. J. Org. Chem. 2005, 552-557.
51. a) C. Amatore, A. Jutand, F. Khalil, M. A. M'Barki, L. Mottier, Or-ganometallics 1993, 12, 3168-3178;
52. b) C. Amatore, A. Jutand, G. Meyer, Inorg. Chim. Acta 1998, 273, 76-84;
53. c) C. Amatore, A. Jutand, Coord. Chem. Rev. 1998, 178-180, 511-528.
54. a) E. Negishi, T. Takahashi, K. Akiyoshi, J. Chem. Soc. Chem. Commun. 1986, 1338-1339;
55. b) M. Bottex, M. Cavicchioli, B. Hart-mann, N. Monteiro, G. Balme, J. Org. Chem. 2001, 66, 175-179.
56. CCDC716213 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.
57. For method of isolation, see: a) J. B. G. Siqueira, M. D. G. B. Zoghbi, J. A. Cabral, W. W. Filho, J. Nat Prod. 1995, 58, 730-732. For reports of syntheses, see:
58. b) Y. Asano, T. Kamikawa, T. Tokor-oyama, Bull. Chem. Soc. Jpn. 1976, 49, 3232-3235;
59. c) O. Miyata, A. Nishiguchi, 1. Ninomiya, T. Naito, Chem. Pharm. Bull. 1996, 44, 1285-1287;
60. d) O. Miyata, A. Nishiguchi, I. Ninomiya, K. Aoe, K. Okamura, T. Naito, J. Org. Chem. 2000, 65, 6922-6931;
61. e) B. Raf-faelli, K. Wähälä, T. Hase, Org. Biomol. Chem. 2006, 4, 331-341;
62. f) D. Enders, J. Kirchhoff, V. Lausberg, Liebigs Ann. 1996, 1361-1366;
63. g) D. Enders, M. Milovanović, Z. Naturforsch. B 2007, 62, 117-120. For a hemisynthesis, see:
64. h) K. Wada, K. Munakata, Tetrahedron Lett. 1970, 11, 2017-2019.
65. a) A. P. Krapcho, Synthesis 1982, 805-822, 893-914;
66. b) A. P. Krap-cho, Arkivoc 2007, 1-53, 54-120.
67. The expected 3,4-trans stereochemistry was secured according to: R. Galeazzi, G. Martelli, G. Mobbili, M. Orena, M. Panagiotaki, Heterocycles 2003, 60, 2485-2498.
68. In a first approach, the reverse sequence alkylation/decarboxylation was studied. Unfortunately, the demethoxycarbonylation of the quaternary center proceeded in very limited yield.
69. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.