Synthesis of Cyclobutanone and Cyclobutenone
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1 Synthesis of Cyclobutanone and Cyclobutenone Salan, J., in Science of Synthesis, 26 (2004),p.557 Ruben Martin, Synthesis, 2013, 45, 563 Penghao Chen Dong Group Seminar Aug, 22 nd, 2013
2 Synthetic Application
3 Cyclobutanone Synthesis Cyclodialkylation by 1,3-Dihalopropanes Seebach, D.; Jones, N. R.; Corey, E. J., J. Org. Chem., 1968, 33, 300. Ogura, K.; Yamashita, M.; Suzuki, M.; Tsuchihashi, G., Tetrahedron Lett., 1974, Possel, O.; van Leusen, A. M., Tetrahedron Lett., 1977, 4229.
4 Cyclobutanone Synthesis Cyclization by Intramolecular Substitution Stork, G.; Depezay, J. C.; d Angelo, J., Tetrahedron Lett., 1975, 389. Klinkmüller, K. D.; Marschall, H.; Weyersthal, P., Chem. Ber., 1975, 108, 191. Hummel, K.; Hanack, M., Justus Liebigs Ann. Chem., 1971, 746, 211.
5 Cyclobutanone Synthesis Ring Formation by Carbonylation Carter, C. A. G.; Greidanus, G.; Chen, J.-X.; Stryker, J. M., J. Am. Chem. Soc., 2001, 123, Hegedus, L. S.; Bates, R. W.; Söderberg, B. C., J. Am. Chem. Soc., 1991, 113, 923. Theopold, K. H.; Becker, R. N.; Bergman, R. G., J. Am. Chem. Soc., 1982, 104, 5250.
6 Cyclobutanone Synthesis [2 + 2] Cycloaddition Brady, W. T.; Parry, F. H.; Stockton, J. D., J. Org. Chem., 1971, 36, Lee, S. Y.; Kulkarni, Y. S.; Burbaum, B. W.; Johnston, M. I.; Snider, B. B., J. Org. Chem., 1988, 53, Jeffs, P. W.; Molina, G.; Cass, M. W.; Cortese, N. A., J. Org. Chem., 1982, 47, Hassner, A.; Pinnick, H. W.; Ansell, J. M., J. Org. Chem., 1978, 43, 1774.
7 Cyclobutanone Synthesis [2 + 2] Cycloaddition Sidani, A.; Marchand-Brynaert, J.; Ghosez, L., Angew. Chem. Int. Ed. Engl., 1974, 13, 267. Amice, P.; Conia, J. M., Tetrahedron Lett., 1974, 479. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S., J. Am. Chem. Soc., 1992, 114, 8869.
8 Cyclobutanone Synthesis [2 + 2] Cycloaddition Quendo, A.; Rousseau, G., Synth. Commun, 1989, 19, Ficini, J.; d Angelo, J.; Eman, A.; Touzin, A. M., Tetrahedron Lett., 1976, 683. Ikeda, M.; Uno, T.; Hamma, K.; Ohno, K.; Tamura, Y., Synth. Commun., 1980, 10, 437.
9 Cyclobutanone Synthesis Ring Enlargement of Three-Membered Ring Conia, J. M.; Salaün, J., Bull. Soc. Chim. Fr., 1964, Barnier, J. P.; Garnier, B.; Girard, C.; Denis, J. M.; Salaün, J.; Conia, J. M., Tetrahedron Lett., 1973, 1747.
10 Cyclobutanone Synthesis Rearrangement of Spiro[2,2]pentanes Salaün, J.; Garnier, B.; Conia, J. M., Tetrahedron, 1974, 30, Braun, M.; Dammann, R.; Seebach, D., Chem. Ber., 1975, 108, Crandall, J. K.; Conower, W. W., J. Org. Chem., 1974, 39, 63.
11 Cyclobutanone Synthesis Rearrangement of (1-hydroxyalkyl)cyclopropane Cohen, T.; Bhupathy, M.; Matz, J. R., J. Am. Chem. Soc., 1983, 105, 520.
12 Cyclobutanone Synthesis Rearrangement of (1-hydroxyalkyl)cyclopropane Trost, B. M.; Keeley, D. E., J. Am. Chem. Soc., 1974, 96, Krief, A., Top. Curr. Chem., 1987, 135, 1. Cohen, T.; Sherbine, T. P.; Matz, J. R.; Hutchins, R. R.; Mc Herny, B. M.; Willey, P. R., J. Am. Chem. Soc., 1984, 106, 3245.
13 Cyclobutanone Synthesis Rearrangement of Cyclopropanol Derivatives Salaün, J.; Conia, J. M., Tetrahedron Lett., 1972, Wasserman, H. H.; Hearn, M. J.; Haveaux, B.; Thyes, M., J. Org. Chem., 1976, 41, 153. Stork, G.; Depezay, J. C.; d Angelo, J., Tetrahedron Lett., 1975, 389.
14 Cyclobutanone Synthesis Rearrangement of (1-Bromoalkylidene)cyclopropanes Caubere, P.; Coudert, G., Bull. Soc. Chim. Fr., 1971, Bässler, T.; Hanack, M., Tetrahedron Lett., 1971, Salaün, J.; Hanack, M., J. Org. Chem., 1975, 40, 1994.
15 Cyclobutanone Synthesis Ring Contraction Smith, A. B., III; Foster, A. M.; Agosta, W. C., J. Am. Chem. Soc., 1972, 94, Zimmerman, H. E.; Solomon, R. D., J. Am. Chem. Soc., 1986, 108, Engel, P. S.; Schexnayder, M. A.; Ziffer, H.; Seeman, J. I., J. Am. Chem. Soc., 1974, 96, 924. Demuth, M.; Raghavan, P. R.; Carter, C.; Nakano, K.; Schaffner, K., Helv. Chim. Acta, 1980, 63, 2434.
16 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and alkyne Danheiser R. L.; Savariar S.; Cha D. D. Organic Syntheses, Coll. 1993, 8, 82; 1990, 68, 32. Wasserman H. H.;Dehmlow E. Tetrahedron Lett. 1962, 3, Kowalski C. J.; Lal G. S. J. Am. Chem. SOC. 1988, 110, 3693.
17 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and alkyne 79% 80% 65% 67%(83%) 86% Kohnen A. L.; Mak X.-Y.; Lam T.-Y.; Dunetz J.-R.; Danheiser R.-L. Tetrahedron, 2006, 62, 3815.
18 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Stevens, R. V.; Bisacchi, G. S. J. Org. Chem. 1982, 47, 2393.
19 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Maurin, P.; Ibrahim-Ouali, M.; Santelli, M. Eur. J. Org. Chem. 2002, 151. Maurin, P.; Ibrahim-Ouali, M.; Santelli, M. Tetrahedron Lett. 2001, 42, Mariet, N.; Ibrahim-Ouali, M.; Santelli, M. Tetrahedron Lett. 2002, 43, 5789.
20 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Im, G. Y. J.; Bronner, S. M. Paton, R. S.;Cheong, P. H. Y.; Houk, K. N.; Garg, N. K. J. Am. Chem.Soc. 2010, 132, Bronner, S. M.; Bahnck, K. B.; Garg, N. K. Org. Lett. 2009, 11, 1007.
21 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Hosoya, T.; Kuriyama, Y.; Suzuki, K. Synlett, 1995, 177. Hamura, T.; Hosoya, T.; Kuriyama, Y.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589.
22 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Hamura, T.; Ibusuki, Y.; Sato, K.; Matsumoto, T.; Osamura, Y.; Suzuki, K. Org. Lett. 2003, 5, 3551.
23 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 3534.
24 Cyclobutenone Synthesis [2+2] type cycloadditions [2 + 2] Cycloaddition by ketene and benzyne Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377.
25 Cyclobutenone Synthesis Metal-mediated intramolecular reactions Metal-Mediated Intramolecular Reactions Aidhen, I. S.; Ahuja, J. R. Tetrahedron Lett. 1992, 33, 5431.
26 Cyclobutenone Synthesis Metal-Catalyzed Cross-Coupling Reactions Metal-Catalyzed Cross-Coupling Reactions Martin, R.; Buchwald, S. L. Org. Lett. 2008, 10, Vo, G. D.; Hartwig, J. F. Angew. Chem. Int. Ed. 2008, 47, Martin, R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2007, 46, Álvarez-Bercedo, P.; Flores-Gaspar, A.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2010, 132, 466.
27 Cyclobutenone Synthesis Metal-Catalyzed Cross-Coupling Reactions Metal-Catalyzed Cross-Coupling Reactions Flores-Gaspar, A.; Gutiérrez-Bonet, A.; Martin, R. Org. Lett. 2012, 14, 5234.
28 Cyclobutenone Synthesis Stille Cross-Coupling Reactions Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org. Chem. 1993, 58, Bradley, J. C.; Durst, T. J. Org. Chem. 1991, 56, 5459.
29 Cyclobutenone Synthesis Tandem Michael Addition/Cyclization Reactions of 2,3-allenoate Chai G.; Wu S.; Fu C.-L.; Ma S.-M. J. Am. Chem. Soc. 2011, 133, 3740
30 Thanks
31 Answers
32 Answers
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