5094
B. Mahmoud, F. G. West / Tetrahedron Letters 48 (2007) 5091–5094
Tetrahedron 2005, 61, 6479–6517; (c) Frontier, A. J.;
Collison, C. Tetrahedron 2005, 61, 7577–7606; (d) Tius, M.
A. Eur. J. Org. Chem. 2005, 2193–2206.
9. Reviews: (a) Trofimov, B. A.; Shainyam, B. A. In The
Chemistry of Sulfur-Containing Functional Groups; Patai,
S., Rappoport, Z., Eds.; Wiley: Chichester, 1993; pp 659–
797; (b) Narasaka, K.; Hayashi, Y. In Advances in
Cycloaddition; Lautens, M., Ed.; JAI Press: Greenwich,
CT, 1997; Vol. 4, pp 87–120.
10. For an elegant example of the use of vinyl sulfide 3+2
reactions in synthesis, see: Mizuno, H.; Domon, K.;
Masuya, K.; Tanino, K.; Kuwajima, I. J. Org. Chem.
1999, 64, 2648–2656.
11. Crystallographic data (excluding structure factors) for the
structures in this Letter have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication no. CCDC 639920. Copies of the data can
be obtained, free of charge, on application to CCDC, 12
Union Road, Cambridge CB2 1EZ, UK, (fax: +44 (0)
1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
12. For a detailed discussion of transition state geometries in
3+2 cycloadditions of allyl cations and vinyl sulfides, see:
(a) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J.
Am. Chem. Soc. 1998, 120, 1724–1731; We have previously
observed alkene trapping of the Nazarov cyclopentenyl
intermediate via an apparent compact transition state: (b)
Bender, J. A.; Blize, A. E.; Browder, C. C.; Giese, S.;
West, F. G. J. Org. Chem. 1998, 63, 2430–2431.
2. (a) Kerr, D. J.; Metje, C.; Flynn, B. L. Chem. Commun.
2003, 1380–1381; (b) Bee, C.; Leclerc, E.; Tius, M. A. Org.
Lett. 2003, 5, 4927–4930; (c) Aggarwal, V. K.; Belfield, A.
J. Org. Lett. 2003, 5, 5075–5078; (d) Liang, G.; Trauner,
D. J. Am. Chem. Soc. 2004, 126, 9544–9545; (e) Mazzola,
R. D., Jr.; White, T. D.; Vollmer-Snarr, H. R.; West, F. G.
Org. Lett. 2005, 7, 2799–2801; (f) Cavalli, A.; Masettim,
M.; Recanatini, M.; Prandi, C.; Guarna, A.; Occiato, E.
G. Chem. Eur. J. 2006, 12, 2836–2845, and references cited
therein.
3. (a) Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A.
M.; West, F. G. Angew. Chem., Int. Ed. 2005, 44, 6546–
6549; (b) Grant, T. N.; West, F. G. J. Am. Chem. Soc.
2006, 128, 9348–9349.
4. Dhoro, F.; Tius, M. A. J. Am. Chem. Soc. 2005, 127,
12472–12473.
5. White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46,
5629–5632.
6. Giese, S.; West, F. G. Tetrahedron 2000, 56, 10221–10228.
7. Azides can also nucleophilically capture the Nazarov
intermediate, but the ultimate products are heterocycles
resulting from subsequent ring-expansion: (a) Rostami,
A.; Wang, Y.; Arif, A. M.; McDonald, R.; West, F. G.
Org. Lett. 2007, 9, 703–706; (b) Song, D.; Rostami, A.;
West, F. G., submitted for publication.
8. (a) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc.
1999, 121, 876–877; (b) Giese, S.; Kastrup, L.; Stiens, D.;
West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970–1973;
(c) Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org.
Lett. 2003, 5, 2747–2750.
13. Padwa, A.; Heidelbaugh, T.; Kuethe, J. J. Org. Chem.
2000, 65, 2368–2378.
14. (a) Fu, R.; Xu, X.; Dang, Q.; Bai, X. J. Org. Chem. 2005,
70, 10810–10816; (b) Blades, K.; Percy, J. Tetrahedron
Lett. 1998, 39, 9085–9088.
15. Sulfoxide elimination product 10 decomposed during
attempted chromatographic purification. The yield given
is for crude material before chromatography.