8510
J. R. Lacey et al. / Tetrahedron Letters 46 (2005) 8507–8511
Dickinson, M. G.; May, S. A.; Pickering, D. A.; Sadek, P.
C. Synthesis 1998, 1133.
(University of Maryland Baltimore County) for useful
discussions.
13. (a) Reglinski, J. In Chemistry of Arsenic, Antimony and
Bismuth; Norman, N. C., Ed.; Blackie Academic and
Professional: New York, 1998; pp 403–440; (b) Organo-
bismuth Chemistry; Suzuki, H., Matano, Y., Eds.; Elsevier:
Amsterdam, 2001.
Supplementary data
14. For recent reviews on use of bismuth(III) compounds in
organic synthesis see: (a) Leonard, N. M.; Wieland, L. C.;
Mohan, R. S. Tetrahedron 2002, 58, 8373; (b) Antoniotti,
S. Synlett 2003, 1566; (c) Gaspard-Iloughmane, H.; Le
Roux, C. Eur. J. Org. Chem. 2004, 2517; For some recent
applications of Bi(OTf)3ÆxH2O as a catalyst in organic
synthesis, see: (d) Anderson, E. A.; Ernat, J. J.; Nguyen,
M. P.; Palma, A. C.; Mohan, R. S. Tetrahedron Lett. 2005,
46, 7747; (e) Anzalone, P. A.; Baru, A. R.; Danielson, E.
M.; Hayes, P. D.; Nguyen, M. P.; Panico, A. F.; Smith, R.
C.; Mohan, R. S. J. Org. Chem. 2005, 70, 2091; (f)
Sreedhar, B.; Swapna, V.; Sridhar, Ch.; Saileela, D.;
Sunitha, A. Synth. Commun. 2005, 35, 1177; (g) Sreedhar,
B.; Swapna, V.; Sridhar, Ch. Catal. Commun. 2005, 6, 293;
(h) Khodaei, M.; Khosorpur, A. R.; Kookhazadeh, M.
Can. J. Chem. 2005, 83, 209; (i) Kamal, A.; Ahmed, S. K.;
Sandbhor, M.; Khan, M. N. A.; Arifuddin, M. Chem.
Lett. 2005, 34, 1142; (j) Yadav, J. S.; Reddy, B. V. S.;
Swamy, T.; Rao, R. K. Tetrahedron Lett. 2004, 45, 6037;
(k) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett
2004, 963; (l) Matsushita, Y.; Sugamoto, K.; Matsui, T.
Tetrahedron Lett. 2004, 45, 4723; (m) Arnold, J. N.;
Hayes, P. D.; Kohaus, R. L.; Mohan, R. S. Tetrahedron
Lett. 2003, 44, 9173.
General experimental section, representative proce-
dures, isolation, and characterization of all reaction
products. Supplementary data associated with this arti-
References and notes
1. (a) Goldsmith, D. J. J. Am. Chem. Soc. 1962, 84, 3913;
More recently the cyclization of geraniolene oxide has
been investigated using MeAlCl2, see: (b) Corey, E. J.;
Sodeoka, M. Tetrahedron Lett. 1991, 32, 7005.
2. (a) van Tamelen, E. E.; Storni, A.; Hessler, E. J.;
Schwartz, M. J. Am. Chem. Soc. 1963, 85, 3295; (b) van
Tamelen, E. E.; Willett, J. D.; Clayton, R. B.; Lord, K. E.
J. Am. Chem. Soc. 1966, 88, 4752; (c) van Tamelen, E. E.;
McCormick, J. P. J. Am. Chem. Soc. 1969, 91, 1847; (d)
van Tamelen, E. E.; Sharpless, K. B. J. Am. Chem. Soc.
1969, 91, 1848; (e) van Tamelen, E. E.; Murphy, J. W. J.
Am. Chem. Soc. 1972, 92, 7204; (f) van Tamelen, E. E.;
Anderson, R. J. J. Am. Chem. Soc. 1970, 94, 8225; (g) van
Tamelen, E. E. Acc. Chem. Res. 1974, 8, 152; (h) van
Tamelen, E. E.; Leiden, T. M. J. Am. Chem. Soc. 1982,
104, 2061.
3. (a) van Tamelen, E. E.; Storni, A.; Hessler, E. J.;
Schwartz, M. A. Bioorg. Chem. 1982, 11, 133; (b) van
Tamelen, E. E.; Nadeau, R. G. Bioorg. Chem. 1982, 11,
197.
4. (a) Fish, P. V.; Sudhakar, A. R.; Johnson, W. S.
Tetrahedron Lett. 1993, 34, 7849; (b) Fish, P. V.; Johnson,
W. S. Tetrahedron Lett. 1994, 35, 1469; (c) Fish, P. V.;
Johnson, W. S. J. Org. Chem. 1994, 59, 2324.
15. We have previously reported a highly catalytic method for
the rearrangement of aryl-substituted epoxides to alde-
hydes and ketones using bismuth triflate, see: (a) Bhatia,
K. A.; Eash, K. J.; Leonard, N. M.; Oswald, M. C.;
Mohan, R. S. Tetrahedron Lett. 2001, 42, 8129; For other
examples of activation of epoxides by bismuth triflate see:
(b) Ollevier, T.; Lavie-Compin, G. Tetrahedron Lett. 2004,
45, 49; (c) Yadav, J. S.; Reddy, B. V. S.; Sateesh, G.
Tetrahedron Lett. 2003, 44, 6501.
16. Based on 1H NMR analysis of the crude reaction product,
we did not observe the formation of any of the cyclized
product 5c. A control experiment with an authentic sample
mixture of 5a/b ruled out the possibility that 4 might form
from either 5a or 5b. A similar control experiment has been
carried out with BF3ÆEt2O as the catalyst.8e
5. Boeckman, R. K.; Bruza, K. J.; Heinrich, G. R. J. Am.
Chem. Soc. 1978, 100, 7101.
6. Morgan, D. J.; Sharpless, K. B. J. Am. Chem. Soc. 1981,
103, 462.
7. Tanis, S. P.; Herrinton, P. M. J. Org. Chem. 1983, 48,
4572.
8. (a) Taylor, S. K.; Hockerman, G. H.; Karrick, G. L.; Lyle,
S. B.; Schramm, S. B. J. Org. Chem. 1983, 48, 2449; (b)
Taylor, S. K.; Davisson, M. E.; Hissom, R. B.; Brown, S.
L.; Pristach, H. A.; Schramm, S. B.; Harvey, S. M. J. Org.
Chem. 1987, 52, 425; (c) Taylor, S. K.; Blankespoor, C. L.;
Harvey, S. M.; Richardson, L. J. J. Org. Chem. 1988, 53,
3309; For a review see: (d) Taylor, S. K. Org. Prep. Proc.
Int. 1992, 24, 245; (e) Taylor, S. K.; May, S. A.; Hopkins,
J. A. Tetrahedron Lett. 1993, 34, 1283.
9. (a) Sharpless, K. B. J. Am. Chem. Soc. 1970, 92, 6999; (b)
van Tamelen, E. E.; Carlson, J. G.; Russell, R. K.;
Zawacky, S. R. J. Am. Chem. Soc. 1981, 103, 4615; (c)
Armstrong, R. J.; Weiler, L. Can. J. Chem. 1986, 64, 584;
(d) Tanis, S. P.; Chuang, Y.-H.; Head, D. B. J. Org. Chem.
1988, 53, 4929.
HO
5c
17. Brezinski, B.; Grech, E.; Malarski, Z.; Sobczyk, L.
J. Chem. Soc., Perkin Trans. 2 1991, 2, 857.
18. We have previously reported that when the rearrangement
of trans-stilbene oxide was carried out with CF3SO3H, the
solution turned red and the product diphenylacetaldehyde
was less pure than that obtained with bismuth triflate.15a
This observation points to the role of bismuth(III) triflate
as a Lewis acid in the rearrangement of epoxides and not
to protic acid catalysis by triflic acid released by hydrolysis
of bismuth triflate. For a discussion on the role of triflic
acid in the metal triflate catalyzed acylation of alcohols,
10. (a) Procter, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.;
Mather, A. N. Tetrahedron 1988, 44, 3953; (b) Pettersson,
L.; Frejd, T. J. Chem. Soc., Perkin. Trans. 1 2001, 789.
11. Maruoka, K.; Murase, N.; Ooi, T.; Yamamoto, H. Synlett
1991, 857.
´
see: (a) Dumeunier, R.; Marko, I. E. Tetrahedron Lett.
2004, 45, 825; (b) Carrigan, M. C.; Freiberg, D. A.; Smith,
R. C.; Zerth, H. M.; Mohan, R. S. Synthesis 2001, 2091.
19. Corey, E. J.; Staas, D. D. J. Am. Chem. Soc. 1998, 120,
3526, Under the acidic conditions employed, the authors
12. One example of an easy-to-handle reagent to promote
epoxy olefin cyclization is NafionÒ-H, see: Taylor, S. K.;