D. R. Bobeck et al. / Tetrahedron Letters 50 (2009) 3145–3147
3147
CO2Et
CO2Et
N3
N
N
O
O
²
H2C
O
O
O
O
N
H
N
N
CO2Et
14
15
13
Ph3P, H2O
CH3
CH2
N
Ph3P
N
H2C
CO2Et
CO2Et
O
N
N
O
N
N
O
O
CO2Et
16
18
17
Scheme 4.
13. Anthoni, U.; Christophersen, C.; Nielson, P. H.. In Alkaloids: Chemical and
Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1999; Vol. 13, pp
163–236.
14. (a) Dounay, A. B.; Humphreys, P. G.; Overman, L. E.; Wrobleski, A. D. J. Am.
Chem. Soc. 2008, 130, 5368; (b) Shen, L.; Zhang, M.; Wu, Y.; Qin, Y. Angew.
Chem., Int. Ed. 2008, 47, 3618.
Acknowledgments
We appreciate the financial support provided by the National
Science Foundation (CHE-0742663). F.C.S. wishes to thank the
Fundación Ramón Areces and the Universidad de Granada, Spain,
for funds to allow for a short research leave at Emory University.
15. Dounay, A. B.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2005, 127,
10186.
16. (a) Grotjahn, D. B.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1990, 112, 5653; (b) Levy,
J.; Sapi, J.; Laronze, J. Y.; Royer, D.; Toupet, L. Synlett 1992, 601.
17. (a) Solé, D.; Peidró, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225; (b) Solé, D.; Diaba, J.;
Bonjoch, J. J. Org. Chem. 2003, 68, 5746; (c) Bonjoch, J.; Diaba, F.; Puigbó, G.;
Peidró, E.; Solé, D. Tetrahedron Lett. 2003, 44, 8387; (d) Solé, D.; Urbaneja, X.;
Bonjoch, J. Adv. Synth. Catal. 2004, 346, 1646; (e) Solé, D.; Urbaneja, X.; Bonjoch,
J. Org. Lett. 2005, 7, 5461.
References and notes
1. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze,
L. F. Chem. Rev. 1996, 96, 115.
2. (a) Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992; (b) Bunce, R. A.
Tetrahedron 1995, 51, 13103; (c) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem.
Rev. 1996, 96, 195.
18. Padwa, A.; Brodney, M. A.; Dimitroff, M.; Liu, B.; Wu, T. J. Org. Chem. 2001, 66,
3119.
19. Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315.
20. Bur, S. K.; Lynch, S. M.; Padwa, A. Org. Lett. 2002, 4, 473.
21. (a) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240; (b) Shen, Q.;
Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
3. Ziegler, F. E.. In Paquette, L. A., Ed.; Comprehensive Organic Synthesis
Combining C–C p-Bonds; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.3,.
4. Waldmann, H. In Domino Reaction in Organic Synthesis Highlight II; Waldmann,
H., Ed.; VCH: Weinheim, 1995; pp 193–202.
5. Curran, D. P.. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.;
Pergamon: Oxford, 1991; Vol. 4, p 779.
22. (a) Sundberg, R. J.; Russell, H. F.; Ligon, W. V.; Lin, L. S. J. Org. Chem. 1972, 37,
719; (b) Murata, S.; Yoshidome, R.; Satoh, Y.; Kato, N.; Tomioka, H. J. Org. Chem.
1995, 60, 1428.
23. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 634; (b) Gololobov, Y. G.;
Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
24. (a) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; (b) Fresneda, P. M.; Molina,
P. Synlett 2004, 1; (c) Wamhoff, H.; Richardt, G.; Stölben, S. Adv. Heterocycl.
Chem. 1995, 64, 159.
6. Wender, P. A., Ed.; Frontiers in Organic Synthesis. Chem. Rev. 1996, 96, 1–600.
7. (a) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088;
(b) Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem. 1998, 63, 5304; (c)
Padwa, A.; Brodney, M. A.; Satake, K.; Straub, C. S. J. Org. Chem. 1999, 64, 4617.
8. Padwa, A.; Wang, Q. J. Org. Chem. 2006, 71, 7391.
9. Zhang, H.; Padwa, A. Org. Lett. 2006, 8, 247.
25. (a) Chan, J.; Faul, M. Tetrahedron Lett. 2006, 47, 3361; (b) Blanco, G.; Quintela, J.
M.; Peinador, C. Synthesis 2008, 1397; (c) Fresneda, P. M.; Molina, P.; Delgado,
S. Tetrahedron 2001, 57, 6197; (d) Sugimori, T.; Okawa, T.; Eguchi, S.; Yashima,
E.; Okamoto, Y. Chem. Lett. 1997, 869; (e) Sugimori, T.; Okamoto, T.; Eguchi, S.;
Kakehi, A.; Yashima, E.; Okamoto, Y. Tetrahedron 1998, 54, 7997.
10. (a) Zhang, H.; Boonsombat, J.; Padwa, A. Org. Lett. 2007, 9, 279; (b) Boonsombat,
J.; Zhang, H.; Chughtai, M. J.; Hartung, J.; Padwa, A. J. Org. Chem. 2008, 73, 3539.
11. Massiot, G.; Thepenier, P.; Jacquier, M. J.; Le Men-Olivier, L.; Delaude, C.
Heterocycles 1989, 29, 1435.
12. Ramirez, A.; Garcia-Rubio, S. Curr. Med. Chem. 2003, 10, 1891.