Intermolecular tandem Pd-catalyzed cross-coupling/[4+4] and [4+2] cycloadditions: A one-pot, five-component assembly of bicyclo[6.4.0] dodecanes

Angewandte Chemie - International Edition

Volumn 44, Issue 21, 2005, Pages 3253-3256

  Lee, Phil Ho ^a   Lee, Kooyeon ^a  

^a Kangwon National University   (South Korea)

Author keywords

Cross coupling; Cycloaddition; Indium; Palladium; Tandem reactions

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; ELECTRONS; MOLECULAR DYNAMICS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOADDITIONS; DIENOPHILES; ELECTRONWITHDRAWING GROUPS; PROPARGYL BROMIDES;

ADDITION REACTIONS;

EID: 20344380475     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461957     Document Type: Article

References (50)

1. N. Hall, Science 1994, 266, 32.
2. a) T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York. 1992;
3. b) T.-L. Ho, Tactics of Organic Synthesis, Wiley-Interscience, New York, 1994, p. 79;
4. 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.
5. a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137;
6. Angew. Chem. Int. Ed. Engl. 1993, 32, 131;
7. b) R. A. Bunce, Tetrahedron 1995, 51, 13103;
8. c) E. Negishi, C. Coperet, S. Ma, S.-H. Liou, F. Liu, Chem. Rev. 1996, 96, 365;
9. d) L. F. Tietze, Chem. Rev. 1996, 96, 115.
10. a) I. Ryu, H. Yamazaki, A. Ogawa, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 1187;
11. b) K. Tsuchii, M. Doi, T. Hirao, A. Ogawa, Angew. Chem. 2003, 115, 3614;
12. Angew. Chem. Int. Ed. 2003, 42, 3490.
13. a) T. Shono, I. Nishiguchi, M. Sasaki, J. Am. Chem. Soc. 1978, 100, 4314;
14. b) K. Takai, T. Ueda, N. Ikeda, T. Moriwake, J. Org. Chem. 1996. 61, 7990;
15. c) K. Takai, N. Matsukawa, A. Takahashi, T. Fujii, Angew. Chem. 1998, 110, 160;
16. Angew. Chem. Int. Ed. 1998, 37, 152;
17. d) J. Terao, K. Saito, S. Nii, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1998, 120, 11822.
18. a) M. Lautens, W. T. Klute, Chem. Rev. 1996. 96, 49;
19. b) L. Yet, Chem. Rev. 2000, 100, 2963:
20. c) S.-I. Ikeda, Acc. Chem. Res. 2000, 33, 511;
21. d) J. Montgomery, Acc. Chem. Res. 2000, 33, 467;
22. e) Y. M. Dong, W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 2448;
23. f) P. A. Wender, G. G. Gamber, M. J. C. Scanio, Angew. Chem. 2001, 113, 4013;
24. Angew. Chem. Int. Ed. 2001, 40, 3895;
25. g) S. Ikeda, J. Synth. Org. Chem. Jpn. 2001. 59, 960;
26. h) L. W. A. van Berkom, G. J. T. Kuster, F. Kalmoua, R. de Gelder, H. W. Scheeren, Tetrahedron Lett. 2003, 44, 5091;
27. i) K. Inanaga, K. Takasu, M. Ihara, J. Am. Chem. Soc. 2004, 126, 1352;
28. j) A. Ajamian, J. L. Gleason, Angew. Chem, 2004, 116, 3842;
29. Angew. Chem. Int. Ed. 2004, 43, 3754.
30. a) T. K. Devon, A. I. Scott, Handbook of Naturally Occurring Compounds, Vol. II, Academic Press, New York, 1972;
31. b) D. J. Faulkner, Nat. Prod. Rep. 1984, 1, 251, 551;
32. D. J. Faulkner, Nat. Prod. Rep. 1986, 3, 1;
33. D. J. Faulkner, Nat. Prod. Rep. 1987, 4, 539;
34. D. J. Faulkner, Nat. Prod. Rep. 1988, 5, 613;
35. c) T. Oishi, Y. Ohtsuka, Studies in Natural Products Chemistry (Ed.: Atta-ur-Rahman), Elsevier, Amsterdam. 1989, p. 73;
36. d) C. J. Moody, Studies in Natural Products Chemistry (Ed.: Atta-ur-Rahman), Elsevier, Amsterdam. 1992, pp. 201-239.
37. K. Lee, D. Seomoon, P. H. Lee, Angew. Chem. 2002, 114, 4057;
38. Angew. Chem. Int. Ed. 2002, 41, 3901.
39. For a review on eight-membered ring carbocycle construction, see: a) N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757;
40. b) S. M. Sieburth, N. T. Cunard, Tetrahedron 1996, 52, 6251;
41. c) G. Mehta, V. Singh, Chem. Rev. 1999, 99, 881.
42. a) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201;
43. b) K. Lee, J. Lee, P. H. Lee, J. Org. Chem. 2002, 67, 8265;
44. c) P. H. Lee, D. Seomoon, K. Lee, S. Kim, H. Kim, H. Kim, E. Shim, M. Lee, S. Lee, M. Kim, M. Sridhar, Adv. Synth. Catal. 2004, 346, 1641.
45. a) M. Murakami, K. Itami, Y. Ito, Angew. Chem. 1998, 110, 3636;
46. Angew. Chem. Int. Ed. 1998, 37, 3418;
47. b) M. Murakami, K. Itami, Y. Ito, Synlett 1999, 951;
48. c) Thermal dimerization of vinylallene: R. Schneider, H. Siegel, H. Hopf, Liebigs Ann. Chem. 1981, 1812.
49. 0, α-bromostyrene and propargyl bromide act as synthons of a vinyl anion and allenyl cation, respectively, to produce a vinyl allene: M. Murakami, K. Thami, Y. Ito, Organometatlics 1999, 18, 1326. (Chemical Equation Presented)
50. The use of 3-bromo-1-butyne produced the corresponding [4+4] adduct in 90% yield. The product consisted of three stereoisomers (1.3:1.0:1.3) with respect to the orientation of the two methyl groups on the exocyclic double bonds.