Pd(II)-Catalyzed cyclogeneration of carbocations: Subsequent rearrangement and trapping under oxidative conditions

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7405-7410

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

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

Author keywords

Carbocations; Carbocycles; Palladium; Polycyclization

Indexed keywords

ALCOHOL; ALKADIENE; ALKENE; PALLADIUM; PHENOL; SULFONAMIDE;

CATALYSIS; CHEMICAL BOND; CONFERENCE PAPER; CYCLIZATION; ELIMINATION REACTION; OXIDATION; PINACOL REARRANGEMENT; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 3342875702     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.023     Document Type: Conference Paper

References (51)

1. Richards J.H., Hendrickson J.B. The Biosynthesis of Steroids, Terpenes, and Acetogenins. 1964;W.A. Benjamin Inc, New York
2. Bartlett P.A. Morrison J.D. Asymmetric Synthesis. Vol. 3:1984;341-409 Academic, New York
3. Ishihara K., Ishibashi H., Yamamoto H. J. Am. Chem. Soc. 124:2002;3647-3655
4. Nakamura S., Ishihara K., Yamamoto H. J. Am. Chem. Soc. 122:2000;8131-8140
5. Nishizawa M., Takenaka H., Hayashi Y. J. Org. Chem. 51:1986;806-813
6. Larock R.C. Organomercury Compounds in Organic Synthesis. 1985;Springer, Berlin
7. Several recent developments in Hg(II) chemistry include (a) enantioselective L*Hg(II) reagents and (b) an enyne carbocyclization that is catalytic in Hg(OTf)2; (a) Kang S.H., Kim M. J. Am. Chem. Soc. 125:2003;4684-4685
8. Nishizawa M., Yadav V.K., Skwarczynski M., Imagawa T.H., Sugihara T. Org. Lett. 5:2003;1609-1611
9. Hegedus L.S. Transition Metals in the Synthesis of Complex Organic Molecules. 1994;University Science Books, Mill Valley, CA
10. Hegedus L.S. Trost B.M. Comprehensive Organic Synthesis. Vol. 4:1991;551-569 Pergamon
11. Hegedus L.S. Trost B.M. Comprehensive Organic Synthesis. Vol. 4:1991;571-583 Pergamon
12. Qian H., Widenhoefer R.A. J. Am. Chem. Soc. 125:2003;2056-2057
13. Wang X., Pei T., Han X., Widenhoefer R.A. Org. Lett. 5:2003;2699-2701
14. Widenhoefer R.A. Acc. Chem. Res. 35:2002;905-913
15. Pei T., Widenhoefer R.A. J. Am. Chem. Soc. 123:2001;11290-11291
16. Yang D., Li J.-H., Gao Q., Yan Y.-L. Org. Lett. 5:2003;2869-2871
17. Toyota M., Rudyanto M., Ihara M. J. Org. Chem. 76:2002;3374-3386
18. Ferreira E.M., Stoltz B.M. J. Am. Chem. Soc. 125:2003;9578-9579
19. For early examples of stoichiometric Pd(II) reactivity see: (a) Trebellas J.C., Olechowski J.R., Jonassen H.B. J. Organomet. Chem. 6:1966;412-420
20. Heimbach P., Molin M. J. Organomet. Chem. 49:1973;477-482
21. Heimbach P., Molin M. J. Organomet. Chem. 49:1973;483-494
22. Brown E.D., Sam T.W., Sutherland J.K., Torre A. J. Chem. Soc., Perkin Trans. 1. 1975;2326-2332
23. Hegedus L.S., Williams R.E., McGuire M.A., Hayashi T. J. Am. Chem. Soc. 102:1980;4973-4979
24. Overman L.E., Knoll F.M. J. Am. Chem. Soc. 102:1980;865-867
25. Overman L.E., Jacobsen E.J. J. Am. Chem. Soc. 104:1982;7225-7231
26. Overman L.E., Renaldo A.F. J. Am. Chem. Soc. 112:1990;3945-3949
27. Overman L.E., Renaldo A.F. Tetrahedron Lett. 24:1983;235-238
28. Hahn C., Cucciolito M.E., Vitagliano A. J. Am. Chem. Soc. 124:2002;9038-9039
29. Wiang W., Widenhoefer R.A. Chem. Commun. 2004;660-661
30. For examples of non-oxidative Pd(II)- and Pt(II)-mediated cation-olefin reactions with pincer-ligated metal complexes, see: Koh J.H., Gagné M.R. Angew. Chem., Int. Ed. 2004;. in press
31. For a recent example of an asymmetric variant using BQ see: Uozumi Y., Kyota H., Kato K., Ogasawara M., Hayashi T. J. Org. Chem. 64:1999;1620-1625
32. Palucki M., Wolfe J.P., Buchwald S.L. J. Am. Chem. Soc. 118:1996;10333-10334
33. Chloride-containing Pd(II)-catalyzed Wacker cyclizations are known to proceed by exo addition of nucleophile, while non-chloride containing catalyst can proceed by endo addition mechanisms, see Hayashi T., Yamasaki K., Mimura M., Uozumi Y. J. Am. Chem. Soc. 126:2004;3036-3037
34. The cis-fused bicyclic furan is known, see: Nishizawa M., Iwamoto Y., Takao H., Imagawa H., Sugihara T. Org. Lett. 2:2002;1685-1687
35. Dinorambrox and 9-epi-dinorambrox, see: Ohloff G., Giersch W., Pickenhagen W., Furrer A., Frei B. Helv. Chim. Acta. 68:1985;2002-2029
36. We assign the trans configuration for entry 5 by analogy
37. Overman L.E., Wolfe J.P. J. Org. Chem. 67:2002;6421-6429
38. Overman L.E. Acc. Chem. Res. 25:1992;352-359
39. House H.O., Gaa C.P., VanDerveer D. J. Org. Chem. 48:1983;1661-1670
40. House H.O., Nomura S.G., VanDerveer D., Wissinger E.J. J. Org. Chem. 51:1986;2408-2416
41. For examples of cis selective pinacol rearrangements, see (a) Trost B.M., Neilsen J.B., Hoogsteen K. J. Am. Chem. Soc. 114:1992;5432-5434
42. Hirst G.C., Howard P.N., Overman L.E. J. Am. Chem. Soc. 111:1989;1514-1515
43. Herrinton P.M., Hopkins M.H., Mishra P., Brown M.J., Overman L.E. J. Org. Chem. 52:1987;3711-3712
44. The stereochemistry of the major diastereomer was unambiguously determined by X-ray methods, see Ref. 17 for additional characterization on both stereoisomers
45. For references related to the alternative oxypalladation-initiated mechanism, see: (a) Hayashi T., Yamasaki K., Mimura M., Uozumi Y. J. Am. Chem. Soc. 126:2004;3036-3037
46. Hosokawa T., Murahashi S.-I. Acc. Chem. Res. 23:1990;49-54
47. Balsells D., Maseras F., Keay B.A., Ziegler T. Organometallics. 23:2004;2784-2796
48. Weider P.R., Hegedus L.S., Asada H., D'Andreq S.V. J. Org. Chem. 50:1985;4276-4281
49. Holt D.A. Tetrahedron Lett. 22:1981;2243-2246
50. Kocienski P., Wadman S., Cooper K. J. Org. Chem. 54:1989;1215-1217
51. Bottino F., Grazia M.D., Finocchiaro P., Fronczek R.R., Mamo A., Pappalardo S. J. Org. Chem. 53:1988;3521-3529