Bornane-2,10-sultam: a highly efficient chiral controller and mechanistic probe for the intermolecular Pauson–Khand reaction

Author:

Vázquez Jordi,Fonquerna Sı́lvia,Moyano Albert,Pericàs Miquel A.,Riera Antoni

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference50 articles.

1. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1971, 36; (b) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977–981; (c) Intramolecular version: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436–5438.

2. Leading reviews on the Pauson–Khand reaction: (a) Pauson, P. L.; Khand, I. U. Ann. N.Y. Acad. Sci. 1977, 295, 2–14; (b) Pauson, P. L. Tetrahedron 1985, 41, 5855–5860; (c) Schore, N. E. Org. React. 1991, 40, 1–90; (d) Schore, N. E. In Comprehensive Organic Synthesis II; Hegedus, S. L., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, pp. 703–739; (e) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911–914; (f) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. II, pp. 491–510; (g) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Recent Res. Dev. Organomet. Chem. 1999, 2, 13–43; (h) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297–341; (i) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263–3283; (j) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589–1595.

3. For representative examples of metal mediated cyclocondensations leading to five-membered carbocycles, see: [Ti] (a) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688–11689; (b) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450–9451; [Zr] (c) Agnel, G.; Negishi, E.-I. J. Am. Chem. Soc. 1991, 113, 7424–7426; [Mo] (d) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027–4030; (e) Kent, J. L.; Wan, H. H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407–2410; (f) Cao, H.; Van Ornum, S. G.; Cook, J. M. Tetrahedron Lett. 2000, 41, 5313–5316; [W] (g) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154–1156; (h) Shiu, Y.-T.; Madhushaw, R. J.; Li, W.-T.; Lin, Y.-C.; Lee, G.-H.; Peng, S.-M.; Liao, F.-L.; Wang, S.-L.; Liu, R. S. J. Am. Chem. Soc. 1999, 121, 4066–4067; (i) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamarı́a, J.; Brillet, C.; Garcı́a-Granda, S.; Piñera-Nicolás, A.; Vázquez, J. T. J. Am. Chem. Soc. 1999, 121, 4516–4517; [Fe] (j) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656–1661; [Ru] (k) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187–6188; (l) Kondo, T.; Nakamura, A.; Okada, T.; Suzuki, N.; Wada, K.; Mitsudo, T. J. Am. Chem. Soc. 2000, 122, 6319–6320; (m) Morisaki, Y.; Kondo, T.; Mitsudo, T. Org. Lett. 2000, 2, 949–952; [Ni] (n) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539–546; (o) Pagés, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449–10461; (p) Zhang, M. H.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498–4499; (q) Garcı́a-Gómez, G.; Moretó, J. M. J. Am. Chem. Soc. 1999, 121, 878–879; [Rh] (r) Ojima, I.; Fracchiolla, D. A.; Donovan, R. J.; Banerji, P. J. Org. Chem. 1994, 59, 7594–7595; (s) Matsuda, I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241–244; (t) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130–4135; (t) Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73–87.

4. Thermal promotion of the cobalt catalyzed intramolecular Pauson-Khand reaction — An alternative experimental protocol for cyclopentenone synthesis

5. Photochemical Promotion of the Intramolecular Pauson−Khand Reaction. A New Experimental Protocol for Cobalt-Catalyzed [2 + 2 + 1] Cycloadditions

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