Catalytic ring expansion adventures

Synlett

Volumn 24, Issue 7, 2013, Pages 787-803

  Njardarson, Jon T ^a  

^a University of Arizona   (United States)

Author keywords

aziridines; catalysis; oxetanes; oxiranes; ring expansion; strained rings; thiiranes

Indexed keywords

1,2 EPOXY 3 BUTENE; ACETYLACETONATE COPPER; ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; CLOPIDOGREL; COUNTERION; CUPRIC ION; GONIOTHALESDIOL; NATURAL PRODUCT; PLATENSIMYCIN; SULFONAMIDE; UNCLASSIFIED DRUG; VARITRIOL; VINYL AZIRIDINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; RING EXPANSION REACTION; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 84874800530     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1318326     Document Type: Article

References (117)

1. Lautens, M.; Ouellet, S. G.; Raeppel, S. Angew. Chem. Int. Ed. 2000, 39, 4079; and references cited therein.
2. Crawford, R. J.; Lutener, S. B.; Cockcroft, R. D. Can. J. Chem. 1976, 54, 3364.
3. Khumtaveeporn, K.; Halper, H. Acc. Chem. Res. 1995, 28, 414.
4. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174.
5. Besozzi, A. J.; Cooley, S. D.; Potts, F. E. III. Petro-Tex Chemical Corporation, Patent US 3812158, 1974; Chem. Abstr. 1974, 81, 41287.
6. Wall, R. G.; Kurkov, V. P. Chevron Research Company, Patent US 3996248, 1976; Chem. Abstr. 1977, 86, 89592.
7. Fischer, M. BASF. Patent US 5034545, 1991; Chem. Abstr. 1991, 115, 30088.
8. Monnier, J. R.; Godleski, S. R.; Low, H. M.; McCullough, L. G.; McGarry, L. W.; Phillips, G. W. Eastman Kodak Company, Patent US 5082956, 1992; Chem. Abstr. 1992, 116, 63473.
9. Olofsson, B.; Somfai, P. Vinylepoxides. Aziridines and Epoxides in Organic Synthesis, In Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006, 315-347.
10. Batory, L. A.; McInnis, C. E.; Njardarson, J. T. J. Am. Chem. Soc. 2006, 128, 16054.
11. -Methyltetrahydrofuran is used as a greener replacement for dichloromethane, see: Ripin, D. H. B.; Vetelino, M. Synlett 2003, 2353
12. Elliott, D. C.; Frye, J. G. Battelle Memorial Institute, Patent US 5883266, 1999; Chem. Abstr. 1999, 130, 211627.
13. Ahmed, I. Pure Energy Corporation, Patent US 6852868 B2, 2005.
14. Weyer, H.-J.; Fischer, R.; Merger, F.; Frank, J.; Henkelmann, J.; Siegel, H.; Ruehl, T. BASF, Patent US 5536854, 1996; Chem. Abstr. 1996, 126, 167776.
15. Takemoto, M.; Abe, T. Mitsubishi Gas Chemical Company, Inc., Patent US 5990324, 1999; Chem. Abstr. 1998, 129, 275832.
16. Manzer, L. E. E. I. Du Pont de Nemours and Company, Patent US 2003/0109724 A1, 2003; Chem. Abstr. 2003, 139, 38256.
17. Beavers, W. A.; Ignatchenko, A. V. Eastman Kodak Company, Patent US 6812354 B2, 2004; Chem. Abstr. 2004, 141, 54185.
18. Vollhardt, K. P. C.; Bergman, R. G. J. Am. Chem. Soc. 1973, 95, 7538.
19. Adams, R. D.; Long, J. W. IV.; Perrin, J. L. J. Am. Chem. Soc. 1998, 120, 1922.
20. Adams, R. D. Acc. Chem. Res. 2000, 33, 171.
21. Larksarp, C.; Sellier, O.; Alper, H. J. Org. Chem. 2001, 66, 3502.
22. Direct thiirinations are possible, although their development is still in the early stages and existing methods are far from being useful, see: Adam, W.; Bargon, R. M. Chem. Rev. 2004, 104, 251.
23. Maciagiewicz, I.; Dybowski, P.; Skowronska, A. Tetrahedron Lett. 1999, 40, 3791.
24. Rogers, E.; Araki, H.; Batory, L. A.; McInnis, C. E.; Njardarson, J. T. J. Am. Chem. Soc. 2007, 129, 2768.
25. For a recent example, see: Fantauzzi, S.; Gallo, E.; Caselli, A.; Piangiolino, C.; Ragaini, F.; Re, N.; Cenini, S. Chem. Eur. J. 2009, 15, 1241.
26. Heine, H. W.; Fetter, M. E.; Nicholson, E. M. J. Am. Chem. Soc. 1959, 81, 2202.
27. Hudlicky, T.; Frazier, J. O.; Kwart, L. D. Tetrahedron Lett. 1985, 26, 3523.
28. Pearson, W. H. Tetrahedron Lett. 1985, 26, 3527.
29. Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje, M.; Seoane, A.; Kwart, L. D.; Beal, C. J. Am. Chem. Soc. 1986, 108, 3755.
30. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K. C.; Poon, Y. F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719.
31. Atkinson, R. S.; Rees, C. W. Chem. Commun. 1967, 1232.
32. Scheiner, P. J. Org. Chem. 1967, 32, 2628.
33. Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749.
34. Hirner, S.; Somfai, P. Synlett 2005, 3099.
35. Fugami, K.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857.
36. Fugami, K.; Miura, K.; Morizawa, Y.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1989, 45, 3089.
37. Ohno, H. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006, 37.
38. Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
39. Carpino, L. A.; Kirkley, R. K. J. Am. Chem. Soc. 1970, 92, 1784.
40. Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530.
41. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
42. Brichacek, M.; Lee, D.; Njardarson, J. T. Org. Lett. 2008, 10, 5023.
43. For a review of 3-pyrroline synthetic approaches, see: Brichacek, M.; Njardarson, J. T. Org. Biomol. Chem. 2009, 7, 1761.
44. Brichacek, M.; Batory, L. A.; Njardarson, J. T. Angew. Chem. Int. Ed. 2010, 49, 1648.
45. Corey, E. J.; Chaykovski, M. J. Am. Chem. Soc. 1962, 84, 867.
46. Darzens, G. Compt. Rend. 1904, 139, 1214.
47. For an example, see: Kang, B.; Britton, R. Org. Lett. 2007, 9, 5083.
48. Brichacek, M.; Villalobos, M. N.; Plichta, A.; Njardarson, J. T. Org. Lett. 2011, 13, 1110.
49. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
50. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
51. Davis, F. A.; Reddy, R. T.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387.
52. Davis, F. A. J. Org. Chem. 2006, 71, 8993.
53. Illa, O.; Arshad, M.; Ros, A.; McGarrigle, E. M.; Aggarwal, V. K. J. Am. Chem. Soc. 2010, 132, 1828.
54. Davis, F. A.; Liu, H.; Zhou, P.; Fang, T.; Reddy, G. V.; Zhang, Y. J. Org. Chem. 1999, 64, 7559.
55. Clard, R. D.; Helmkamp, G. K. J. Org. Chem. 1964, 29, 1316.
56. Muller, R. K.; Felix, D.; Schreiber, J.; Eschenmosher, A. Helv. Chim. Acta 1970, 53, 1479.
57. Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563.
58. McGrath, N. A.; Bartlett, E. S.; Sittihan, S.; Njardarson, J. T. Angew. Chem. Int. Ed. 2009, 48, 8543.
59. Wang, J.; Soisson, S. M.; Young, K.; Shoop, W.; Kodali, S.; Galgoci, A.; Painter, R.; Parthasarathy, G.; Tang, Y. S.; Cummings, R.; Ha, S.; Dorso, K.; Motyl, M.; Jayasuriya, H.; Ondeyka, J.; Herath, K.; Zhang, C.; Hernandez, L.; Allocco, J.; Basilio, A.; Tormo, J. R.; Genilloud, O.; Vicente, F.; Pelaez, F.; Colwell, L.; Lee, S. H.; Michael, B.; Felcetto, T.; Gill, C.; Silver, L. L.; Hermes, J. D.; Bartizal, K.; Barrett, J.; Schmatz, D.; Becker, J. W.; Cully, D.; Singh, S. B. Nature 2006, 441, 358.
60. McGrath, N. A.; Lee, C. A.; Araki, H.; Brichacek, M.; Njardarson, J. T. Angew. Chem. Int. Ed. 2008, 47, 9450.
61. Morton, J. G. M.; Kwon, L. D.; Freeman, J. D.; Njardarson, J. T. Tetrahedron Lett. 2009, 50, 1684.
62. Morton, J. G. M.; Kwon, L. D.; Freeman, J. D.; Njardarson, J. T. Synlett 2009, 23.
63. Morton, J. G. M.; Dragichi, C.; Kwon, L. D.; Njardarson, J. T. Org. Lett. 2009, 11, 4492.
64. McGrath, N. A.; Binner, J. R.; Markopoulos, G.; Brichacek, M.; Njardarson, J. T. Chem. Commun. 2011, 47, 209.
65. Molander, G. A.; Petrillo, D. E. Org. Lett. 2008, 10, 1795.
66. Li, C.; Pace, E. A.; Liang, M.-C.; Lobkovsky, E.; Gilmore, T.; Porco, J. A. Jr. J. Am. Chem. Soc. 2001, 123, 11308.
67. Gevorgyan, V.; Liu, J.-X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 8919.
68. Lalic, G.; Corey, E. J. Org. Lett. 2007, 9, 4921.
69. Tiefenbacher, K.; Mulzer, J. Angew. Chem. Int. Ed. 2007, 46, 8074.
70. Cao, S.-G.; Wu, X.-H.; Sim, K.-Y.; Tan, B. K. H.; Pereira, J. T.; Goh, S.-H. Tetrahedron 1998, 54, 2143.
71. Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. E. J. Am. Chem. Soc. 2005, 127, 6964.
72. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
73. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
74. Malmstrom, J.; Christophersen, C.; Barrero, A. F.; Oltra, J. E.; Justicia, J.; Rosales, A. J. Nat. Prod. 2002, 65, 364.
75. Brichacek, M.; Batory, L. A.; McGrath, N. A.; Njardarson, J. T. Tetrahedron 2010, 66, 4832.
76. For a Julia olefination example employing a similar sulfone, see: Esteban, J.; Costa, A. M.; Vilarrasa, J. Org. Lett. 2008, 10, 4843.
77. Mack, D. J.; Njardarson, J. T. Angew. Chem. Int. Ed. 2013, 52, 1543.
78. De Pascual Teresa, J.; San Feliciano, A.; Barrero, A. F. An. Quim. 1973, 69, 1065.
79. Barrero, A. F.; Herrador, M. M.; Arteaga, P.; Arteaga, J. F.; Arteaga, A. F. Molecules 2012, 17, 1448.
80. Barrero, A. F.; Rafael, Q. M.; Altarejos, J. C. Tetrahedron 1991, 47, 4441.
81. Shi, Y. Acc. Chem. Res. 2004, 37, 488.
82. Nunez, C. V.; Amendola, M. C.; Henrique, J.; Lago, G.; Roque, N. F. Biochem. Sys. Eco. 2004, 32, 233.
83. Iwamoto, M.; Ohtsu, H.; Tokuda, H.; Nishino, H.; Matsunaga, S.; Tanaka, R. Bioorg. Med. Chem. 2001, 9, 1911.
84. Li, Y.-C.; Kuo, Y.-H. Chem. Pharm. Bull. 2002, 50, 498.
85. Minami, T.; Iwamoto, M.; Ohtsu, H.; Ohishi, H.; Tanaka, R.; Yoshitake, A. Planta Med. 2002, 68, 742.
86. Wang, Y.-Z.; Tang, C.-P.; Ke, C.-Q.; Weiss, H.-C.; Gesing, E.-R.; Ye, Y. Phytochemistry 2008, 69, 518.
87. De Clercq, P. J. Chem. Rev. 1997, 97, 1755.
88. Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 2765.
89. Herbert, J. M.; Frehel, D.; Valee, E.; Kieffer, G.; Gouy, D.; Berger, Y.; Necciari, J.; Defreyn, G.; Maffrand, J. P. Cardiovasc. Drug Rev. 1993, 11, 180
90. Wohl, A.; Losanitsch, M. S. Ber. Dtsch. Chem. Ges. 1908, 40, 4685.
91. Sadhu, K. M.; Matteson, D. S. Tetrahedron Lett. 1986, 27, 795.
92. Rossy, P. A.; Hoffmann, W.; Muller, N. J. Org. Chem. 1980, 45, 617.
93. Carroll, A. R.; Pierens, G. K.; Fechner, G.; Leone, P. A.; Ngo, A.; Simpson, M.; Hyde, E.; Hooper, J. N. A.; Bostrom, S.-L.; Musil, D.; Quinn, R. J. J. Am. Chem. Soc. 2002, 124, 13340.
94. Mack, D. J.; Njardarson, J. T. Chem. Sci. 2012, 3, 3321.
95. Pawlowski, V.; Kunkely, H.; Zabel, M.; Vogler, A. Inorg. Chim. Acta 2004, 357, 824.
96. Okazawa, A.; Ishida, T.; Nogami, T. Polyhedron 2005, 24, 2584.
97. Gurevich, M. Z.; Sas, T. M.; Mazepova, Z. V. V.; Stepin, B. D. Zh. Neorg. Khim. 1975, 20, 735.
98. Kitko, D. J.; Wiegers, K. E.; Smith, S. G.; Drago, R. S. J. Am. Chem. Soc. 1977, 99, 1410.
99. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
100. For an example of cobaltocene being used to reduce copper(II) species to copper
101. Bond, A. M.; Khalifa, M. A. Inorg. Chem. 1987, 26, 413.
102. Jakubowski, W.; Matyjaszewski, K. Macromolecules 2005, 38, 4139.
103. Mahesh, M.; Murphy, J. A.; LeStrat, F.; Wessel, H. P. Beilstein J. Org. Chem. 2009, 5, 1.
104. Mustard, T. J. L.; Mack, D. J.; Njardarson, J. T.; Cheong, P. H.-Y. J. Am. Chem. Soc. 2013, 135, 1471.
105. Graddon, D. P.; Ong, W. K. Aust. J. Chem. 1974, 27, 741.
106. Rorabacher, D. B. Chem. Rev. 2004, 104, 651.
107. Rutjes, F. P. J. T.; Tjen, K. C. M.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717.
108. Wang, C.; Tunge, J. A. Org. Lett. 2006, 8, 3211.
109. Dubovyk, I.; Pichugin, D.; Yudin, A. K. Angew. Chem. Int. Ed. 2011, 50, 5924.
110. Guo, B.; Schwarzwalder, G.; Njardarson, J. T. Angew. Chem. Int. Ed. 2012, 51, 5675.
111. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
112. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
113. Akiyama, T. Chem. Rev. 2007, 107, 5744.
114. Rueping, M.; Nachtsheim, B. J.; Leawsuwan, W.; Atodiresei, I. Angew. Chem. Int. Ed. 2011, 50, 2.
115. Rueping, M.; Uria, U.; Lin, M.-Y.; Atodieresei, I. J. Am. Chem. Soc. 2011, 133, 3732.
116. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
117. Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626.