Highly regioselective synthesis of spirocyclic compounds by a palladium-catalyzed intermolecular tandem reaction

Angewandte Chemie - International Edition

Volumn 46, Issue 37, 2007, Pages 7068-7071

  Bi, Hai Peng ^a   Liu, Xue Yuan ^a   Gou, Fa Rong ^a   Guo, Li Na ^a   Duan, Xin Hua ^a   Shu, Xing Zhong ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Cyclization; Palladium; Spiro compounds; Tandem reactions

Indexed keywords

CATALYSIS; CYCLIZATION; PALLADIUM; REACTION KINETICS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

SPIRO COMPOUNDS; SPIROCYCLIC COMPOUNDS; TANDEM REACTIONS;

PHENOLS;

EID: 34848888306     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702238     Document Type: Article

References (71)

1. a) B. M. Trost, Science 1991, 254, 1471-1477;
2. b) N. Hall, Science 1994, 266, 32-34;
3. c) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
4. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
5. d) B. M. Trost, M. J. Krische, Synlett 1998, 1-16.
6. a) T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York, 1992;
7. b) T.-L. Ho, Tactics of Organic Synthesis, Wiley-Interscience, New York, 1994, p. 79;
8. c) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds: F. Vögtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, p. 39;
9. d) T. J. J. Muller, Topics in Organometallic Chemistry, Springer, Heidelberg, 2006, 19, pp. 149-205.
10. a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
11. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
12. b) R. A. Bunce, Tetrahedron 1995, 51, 13103-13159;
13. c)L.F. Tietze, Chem. Rev. 1996, 96, 115-136;
14. d) E. Negishi, C. Coperet, S. Ma, S.-H. Liou, F. Liu, Chem. Rev. 1996, 96, 365-394.
15. a) I. Ryu, H. Yamazaki, A. Ogawa, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 1187-1189;
16. b) K. Tsuchii, M. Doi, T. Hirao, A. Ogawa, Angew. Chem. 2003, 115, 3614-3617;
17. Angew. Chem. Int. Ed. 2003, 42, 3490-3493.
18. a) T. Shono, I. Nishiguchi, M. Sasaki, J. Am. Chem. Soc. 1978, 100, 4314-4315;
19. b) K. Takai, T. Ueda, N. Ikeda, T. Moriwake, J. Org. Chem. 1996, 61, 7990-7991;
20. c) K. Takai, N. Matsukawa, A. Takahashi, T. Fujii, Angew. Chem. 1998, 110, 160-163;
21. Angew. Chem. Int. Ed. 1998, 37, 152-155;
22. d) J. Terao, K. Saito, S. Nii, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1998, 120, 11 822-11 823.
23. a) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
24. b) L. Yet, Chem. Rev. 2000, 100, 2963-3008;
25. c) J. Montgomery, Acc. Chem. Res. 2000, 33, 467-473;
26. d) S.-I. Ikeda, Acc. Chem. Res. 2000, 33, 511-519;
27. e) Y. M. Dong, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 2448-2449;
28. f) P. A. Wender, G. G. Gamber, M. J. C. Scanio, Angew. Chem. 2001, 113, 4013-4015;
29. Angew. Chem. Int. Ed. 2001, 40, 3895-3897;
30. g) L. W. A. van Berkom, G. J. T. Kuster, F. Kalmoua, R. de Gelder, H. W. Scheeren, Tetrahedron Lett. 2003, 44, 5091-5093;
31. h) K. Inanaga, K. Takasu, M. Ihara, J. Am. Chem. Soc. 2004, 126, 1352-1353;
32. i) A. Ajamian, J. L. Gleason, Angew. Chem. 2004, 116, 3842-3848;
33. Angew. Chem. Int. Ed. 2004, 43, 3754-3760;
34. j) P. H. Lee, K. Lee, Angew. Chem. 2005, 117, 3317-1320;
35. Angew. Chem. Int. Ed. 2005, 44, 3253-3256.
36. a) T. K. Devon, A. I. Scott, Handbook of Naturally Occurring Compounds, Vol. II, Academic Press, New York, 1972;
37. b) D. J. Faulkner, Nat. Prod. Rep. 1984, 1, 251-280, 551-598;
38. c) D. J. Faulkner, Nat. Prod. Rep. 1986, 3, 1-33;
39. d) D. J. Faulkner, Nat. Prod. Rep. 1987, 4, 539-576;
40. e) D. J. Faulkner, Nat. Prod. Rep. 1988, 5, 613-663;
41. f) T. Oishi, Y. Ohtsuka, Studies in Natural Products Chemistry (Ed: Atta-ur-Rahman), Elsevier, Amsterdam, 1989, p. 73;
42. g) C. J. Moody, Studies in Natural Products Chemistry (Ed: Atta-ur-Rahman), Elsevier, Amsterdam, 1992, pp. 201-239.
43. a) R. C. Larock, N. G. Berrios-Pena, C. A. Fried, J. Org. Chem. 1991, 56, 2615-2617;
44. b) R. Grigg, I. Köppen, M. Rasparini, V. Sridharan, Chem. Commun. 2001, 964-965;
45. c) W. Kazuhiro, K. Hiroi, Heterocycles 2003, 59, 453-457;
46. d) K. Inamoto, A. Yamamoto, K. Ohsawa, K. Hiroya, T. Sakamoto, Chem. Pharm. Bull. 2005, 53, 1502-1507.
47. a) L.-N. Guo, X.-H. Duan, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2006, 71, 3325-3327;
48. b) X.-H. Duan, L.-N. Guo, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2006, 8, 3053-3056;
49. c) X.-H. Duan, L.-N. Guo, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2006, 8, 5777-5780;
50. d) L.-N. Guo, X.-H. Duan, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2007, 72, 1538-1540;
51. e) H.-P. Bi, L.-N. Guo, X.-H. Duan, F.-R. Gou, S.-H. Huang, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2007, 9, 397-400.
52. For cases where the velocity of oxidative addition of the aryl halide to the palladium(0) catalyst is faster than decarboxylation of a propargylic compound, see: X.-H. Duan, X.-Y. Liu, L.-N. Guo, M.-C. Liao, W.-M. Liu, Y.-M. Liang, J. Org. Chem. 2005, 70, 6980-6983.
53. For reviews of the Heck reaction, see: a) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506;
54. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
55. b) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423-1430;
56. c) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7;
57. d) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395.
58. The reaction of purified 4a with 2-iodophenol (2a) was also attempted using the method reported by Larock et al., but a lower yield was obtained; see ref. [8a].
59. a) M. Yoshida, Y. Morishita, M. Fujita, M. Ihara, Tetrahedron Lett. 2004, 45, 1861-1864;
60. b) M. Yoshida, Y. Morishita, M. Fujita, M. Ihara, Tetrahedron 2005, 61, 4381-4393.
61. Y. Kozawa, M. Mori, J. Org. Chem. 2003, 68, 8068-8074.
62. a) I. Shimizu, J. Tsuji, Chem. Lett. 1984, 233-236;
63. b) R. C. Larock, S. Varaprath, H. H. Lau, C. A. Fellows, J. Am. Chem. Soc. 1984, 106, 5274-5284;
64. c) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1984, 25, 4505-4508;
65. d) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1985, 26, 3795-3798;
66. e) M. Ahmar, J.-J. Barieux, B. Cazes, J. Gore, Tetrahedron 1987, 43, 513-526;
67. f) M. Ahmar, B. Cazes, J. Gore, Tetrahedron 1987, 43, 3453-3463;
68. g) B. Cazes, V. Colovray, J. Gore, Tetrahedron Lett. 1988, 29, 627-630;
69. h) B. Frieaa, B. Cazes, J. Gore, Tetrahedron Lett. 1988, 29, 4089-4092;
70. i) N. Kopola, B. Friess, B. Cazes, J. Gore, Tetrahedron Lett. 1989, 30, 3963-3966.
71. R. C. Larock, J. Organomet. Chem. 1999, 576, 111-124.