PdII- and PtII-mediated polycyclization reactions of 1,5- and 1,6-bienes: Evidence in support of carbocation intermediates

Angewandte Chemie - International Edition

Volumn 43, Issue 26, 2004, Pages 3459-3461

  Koh, Jeong Hwan ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

Carbocations; Carbocycles; Cyclization; Palladium; Platinum

Indexed keywords

COMPLEXATION; OLEFINS; PHENOLS; POSITIVE IONS; REACTION KINETICS;

CARBOCATION; HETEROATOMS; PINACOL; POLYCYCLIZATION;

PALLADIUM COMPOUNDS;

ALKENE DERIVATIVE; CARBON; CATION; PALLADIUM COMPLEX; PHENOL DERIVATIVE; PLATINUM DERIVATIVE;

ARTICLE; ATOM; CYCLIZATION; DIASTEREOISOMER; PINACOL REARRANGEMENT;

EID: 4444225192     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453913     Document Type: Article

References (39)

1. P. A. Bartlett in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984, p. 341.
2. K. U. Wendt, G. E. Schultz, E. J. Corey, D. R. Liu, Angew. Chem. 2000, 112, 2930; Angew. Chem. Int. Ed. 2000, 39, 2812.
3. K. U. Wendt, G. E. Schultz, E. J. Corey, D. R. Liu, Angew. Chem. 2000, 112, 2930; Angew. Chem. Int. Ed. 2000, 39, 2812.
4. B. M. Fraga, Nat. Prod. Rep. 2003, 20, 392.
5. See for example: a) K. Ishihara, H. Ishibashi, H. Yamamoto, J. Am. Chem. Soc. 2002, 124, 3647;
6. b) S. Nakamura, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8131.
7. Catalytic antibodies show some asymmetric tendencies: J. Hasserodt, K. D. Janda, R. A. Lerner, J. Am. Chem. Soc. 2000, 122, 40.
8. a) L. E. Overman, F. M. Knoll, J. Am. Chem. Soc. 1980,102,865;
9. b) L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engl. 1984, 23, 579;
10. b) L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engl. 1984, 23, 579;
11. L. E. Overman, E. J. Jacobsen, J. Am. Chem. Soc. 1982, 104, 7225.
12. a) T. Pei, X. Wang, R. A. Widenhoefer, J. Am. Chem. Soc. 2003, 125, 648;
13. b) X. Wang, T. Pei, X. Han, R. A. Widenhoefer, Org. Lett. 2003, 5, 2699;
14. c) T. Pei, R. A. Widenhoefer, Chem. Commun. 2002, 650;
15. d) T. Pei, R. A. Widenhoefer, J. Am. Chem. Soc. 2001, 123, 11290.
16. M. Toyota, M. Rudyanto, M. Ihara, J. Org. Chem. 2002, 67, 3374.
17. In certain instances cyclohexene products were also observed: L. E. Overman, A. F. Renaldo, Tetrahedron Lett. 1983, 24, 2235.
18. X. Wang, R. A. Widenhoefer, Chem. Commun. 2004, 660.
19. L. E. Overman, A. F. Renaldo, J. Am. Chem. Soc. 1990, 112, 3945.
20. For a review of 1,6-diene carbocyclization mechanisms, see: G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215.
21. C. Hahn, M. E. Cucciolito, A. Vitagliano, J. Am. Chem. Soc. 2002, 124, 9038.
22. 2+- activated alkenes: a) C. Hahn, P. Morvillo, E. Herdtweck, A. Vitagliano, Organometallics 2002, 21, 1807;
23. b) C. Hahn, P. Morvillo, A. Vitagliano, Eur. J. Inorg. Chem. 2001, 419;
24. c) C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060.
25. M. Nishizawa, H. Takenaka, Y. Hayashi, J. Org. Chem. 1986, 51, 806.
26. a) L. S. Hegedus in Comprehensive Organic Synthesis, Vol. 4 (Ed.: B. M. Trost), Pergamon Press, 1991, p. 571;
27. b) L. S. Hegedus in Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, California, 1994, p. 199.
28. c) J. J. Becker, L. J. V. Orden, P. S. White, M. R. Gagné, Org. Lett. 2002, 727.
29. The benzylic CH groups are diagnostic: Δδ = 0.78 ppm for cis, and δδ = 0.15 ppm for trans. M. Palucki, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 10333.
30. This information would necessarily be lost if β-hydride elimination or β-fragmentation [Eq. (1)] were operative.
31. a) G. Stork, A. W. Burghstahler, J. Am. Chem. Soc. 1955, 77, 5068;
32. b) A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni, Helv. Chim. Acta 1955, 38, 1890-1904.
33. 4.
34. CCDC-230057 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
35. W. S. Johnson, A. van der Gen, J. J. Swoboda, J. Am. Chem. Soc. 1967, 89, 170.
36. For a recent example, see: J. R. Seiders II, L. Wang, P. E. Floreancig, J. Am. Chem. Soc. 2003, 125, 2406.
37. D. J. Coveney in Comprehensive Organic Synthesis, Vol. 3 (Ed.: G. Pattenden), Pergamon, New York, 1991, p. 777.
38. a) L. E. Overman, J. P. Wolfe, J. Org. Chem. 2002, 67, 6421;
39. b) L. E. Overman, Acc. Chem. Res. 1992, 25, 352.