Dimerization and isomerization reactions of α-lithiated terminal aziridines

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 10009-10021

  Hodgson, David M ^a   Humphreys, Philip G ^a   Miles, Steven M ^a   Brierley, Christopher A J ^a   Ward, John G ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERIZATION; ESTERS; ISOMERIZATION; REACTION KINETICS;

DIASTEREOSELECTIVE CYCLOPROPANATION; TERMINAL AZIRIDINES;

AMINES;

AZIRIDINE DERIVATIVE; ESTER DERIVATIVE; HEXANE;

ARTICLE; CYCLOPROPANATION; DIMERIZATION; ISOMERIZATION; STEREOCHEMISTRY;

EID: 37549039127     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701901t     Document Type: Article

References (116)

1. (a) Deyrup, J. A. In Chemistry of Heterocyclic Compounds; Vol. 42: Small Ring Heterocycles; Pt. 1: Aziridines, Azirines, Thiiranes, Thiirenes; Hassner, A., Ed.; Wiley-VCH: Chichester, UK, 1983; pp 1-214.
2. (b) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258.
3. (a) Wessig, P.; Schwarz, J. Synlett 1997, 893-894.
4. (b) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844-6845.
5. (c) Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952-3954.
6. (d) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 3973-3975.
7. (a) Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
8. (b) Singh, G. S.; D'hooghe, M.; De Kimpe, N. Chem. Rev. 2007, 107, 2080-2135.
9. For recent reviews of lithiated epoxide and aziridine chemistry, see: (a) Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry. Florio, S., Ed. Tetrahedron 2003, 59, 9683-9864.
10. (b) Chemla, F.; Vrancken, E. In The Chemistry of Organolithium Reagents; Rappoport, Z., Marek, I., Eds.; Wiley and Sons: New York, 2004; pp 1165-1242.
11. (c) Hodgson, D. M.; Bray, C. D. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006; pp 145-184.
12. (d) Hodgson, D. M.; Bray, C. D.; Humphreys, P. G. Synlett 2006, 1-22.
13. (e) Hodgson, D. M.; Humphreys, P. G.; Hughes, S. P. Pure. Appl. Chem. 2007, 79, 269-280.
14. Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
15. (a) Arjona, O.; Menchaca, R.; Plumet, J. Heterocycles 2001, 55, 5-7.
16. (b) Müller, P.; Nury, P. Helv. Chim. Acta 2001, 84, 662-677.
17. (c) O'Brien, P.; Rosser, C. M.; Caine, D. Tetrahedron Lett. 2003, 44, 6613-6615.
18. (d) Müller, P.; Riegert, D.; Bernardinelli, G. Helv. Chim. Acta 2004, 87, 227-239.
19. (a) Moore, S. P.; Coote, S. C.; O'Brien, P.; Gilday, J. Org. Lett. 2006, 8, 5145-5148.
20. (b) Hodgson, D. M.; Stefane, B.; Miles, T. J.; Witherington, J. J. Org. Chem. 2006, 71, 8510-8515.
21. Huang, J.; O'Brien, P. Chem. Commun. 2005, 5696-5698.
22. Vedejs, E.; Moss, W. O. J. Am. Chem. Soc. 1993, 115, 1607-1608.
23. (a) Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941-6942.
24. (b) Vedejs, E.; Bhanu Prasad, A. S.; Kendall, J. T.; Russel, J. S. Tetrahedron 2003, 59, 9849-9856.
25. (c) Concellón, J. M.; Ramón Suárez, J.; García-Granda, S.; Díaz, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
26. (d) Concellón, J. M.; Bernad, P. L.; Ramón Suárez, J. Chem. Eur. J. 2005, 11, 4492-4501.
27. During manuscript preparation, an example of terminal aziridine α-lithiation was reported, see: Luisi, R.; Capriati, V.; Di Cunto, P.; Florio, S.; Mansueto, R. Org. Lett. 2007, 9, 3295-3298.
28. Ratio not reported, in our hands a 1.7:1 trans/cis ratio was obtained.
29. Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M. J. Org. Chem. 1994, 59, 276-277.
30. Hodgson, D. M.; Humphreys, P. G.; Xu, Z.; Ward, J. G. Angew. Chem., Int. Ed. 2007, 46, 2245-2248.
31. Hodgson, D. M.; Miles, S. M. Angew. Chem., Int. Ed. 2006, 45, 935-938.
32. Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2006, 8, 995-998.
33. (a) Hodgson, D. M.; Reynolds, N. J.; Coote, S. J. Tetrahedron Lett. 2002, 43, 7895-7897.
34. (b) Hodgson, D. M.; Kirton, E. H. M.; Miles, S. M.; Norsikian, S. L. M.; Reynolds, N. J.; Coote, S. J. Org. Biomol. Chem. 2005, 3, 1893-1904.
35. Śliwińska, A.; Zwierzak, A. Tetrahedron 2003, 59, 5927-5934.
36. Hodgson, D. M.; Humphreys, P. G.; Ward, J. G. Org. Lett. 2005, 7, 1153-1156.
37. (a) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93-124.
38. (b) Lee, W. K.; Ha, H.-J. Aldrichim. Acta 2003, 36, 57-63.
39. (c) Zhou, P.; Chen, B.-C.; Davis, F. A. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006; pp 73-115.
40. (a) Vogel, C. Synthesis 1997, 497-505.
41. (b) Kise, N.; Ozaki, H.; Terui, H.; Ohya, K.; Ueda, N. Tetrahedron Lett. 2001, 42, 7637-7639.
42. (c) Kells, K. W.; Ncube, A.; Chong, J. M. Tetrahedron 2004, 60, 2247-2257.
43. (d) Dieltiens, N.; Stevens, C. V.; Masschelein, K. G. R.; Rammeloo, T. Tetrahedron 2005, 61, 6749-6756.
44. (e) Capriati, V.; Florio, S.; Luisi, R.; Musio, B. Org. Lett. 2005, 7, 3749-3752.
45. Fraser, R. R.; Mansour, T. S. J. Org. Chem. 1984, 49, 3442-3443.
46. Mordini, A.; Peruzzi, D.; Russo, F.; Valacchi, M.; Reginato, G.; Brandi, A. Tetrahedron 2005, 61, 3349-3360.
47. See the Supporting Information for details.
48. TBS protected alcohol 9c has the potential to serve as a useful intermediate in the synthesis of the aziridine-containing antibiotic (2S,3S)-dicarboxyaziridine, isolated from a Streptomyces strain in 1975, see: Naganawa, H.; Usui, N.; Takita, T.; Hamada, M.; Umezwa, H. J. Antiobiot. 1975, 28, 828-829.
49. Mordini, A.; Russo, F.; Valacchi, M.; Zani, L.; Degl'Innocenti, A.; Reginato, G. Tetrahedron 2002, 58, 7153-7163.
50. Reaction of aziridine 10 alone gave aziridinylester 11 in 86% yield.
51. (a) Eisch, J. J.; Kovacs, C. A. J. Organomet. Chem. 1971, 30, C97-C100.
52. (b) Eisch, J. J.; Dua, S. K.; Kovacs, C. A. J. Org. Chem. 1987, 52, 4437-4444.
53. Gawley, R. E.; O'Connor, S.; Klein, R. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Snieckus, V., Ed.; Thieme: Stuttgart, Germany, 2005; Vol. 8a, pp 677-758.
54. Chen, G.; Sasaki, M.; Li, X.; Yudin, A. K. J. Org. Chem. 2006, 71, 6067-6073.
55. Davis, F. A.; Deng, J.; Zhang, Y.; Haltiwanger, R. C. Tetrahedron 2002, 58, 7135-7143.
56. Enantioselective Synthesis of β-Amino Acids; 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley: New York, 2005.
57. (a) Stapley, E. O.; Hendlin, D.; Jackson, M.; Miller, A. K.; Hernandez, S.; Mata, J. M. J. Antibiot. 1971, 24, 42-47.
58. (b) Miller, T. W.; Tristram, E. W.; Wolf, F. J. J. Antibiot. 1971, 24, 48-50.
59. Gentilucci, L.; Grijzen, Y.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 4665-4668.
60. (a) Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; Manuel de los Santos, J. Eur. J. Org. Chem. 2001, 2401-2414.
61. (b) Palacios, F.; Ochoa de Retana, A. M.; Martinez de Marigorta, E.; Manuel de los Santos, J. Org. Prep. Proced. Int. 2002, 34, 219-269.
62. (a) Sun, P.; Weinreb, S. M.; Shang, M. J. J. Org. Chem. 1997, 62, 8604-8608.
63. (b) Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783-786.
64. Hodgson, D. M.; Bray, C. D.; Kindon, N. D. J. Am. Chem. Soc. 2004, 126, 6870-6871.
65. Luisi, R.; Capriati, V.; Florio, S.; Di Cunto, P.; Musio, B. Tetrahedron 2005, 61, 3251-3260.
66. Hodgson, D. M.; Bray, C. D.; Kindon, N. D. Org. Lett. 2005, 7, 2305-2308.
67. (a) Quast, H.; Weise Vélez, C. A. Angew. Chem., Int. Ed. 1974, 13, 342-343.
68. (b) Dimerization of N-unprotected aziridines under Lewis acid catalysis to give aminoaziridines is known, see: Caiazzo, A.; Dalili, S.; Yudin, A. K. Synlett 2003, 2198-2202.
69. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159-2231.
70. (a) Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science 1994, 263, 380-384.
71. (b) Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmet, G. C. J. Org. Chem. 1996, 61, 444-450.
72. (c) Nugiel, D. A.; Jacobs, K.; Worley, T.; Patel, M.; Kaltenbach, R. F., III; Meyer, D. T.; Jadhav, P. K.; De Lucca, G. V.; Smyser, T. E.; Klabe, R. M.; Bacheler, L. T.; Rayner, M. M.; Seitz, S. P. J. Med. Chem. 1996, 39, 2156-2169.
73. (d) Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; DeLucca, G. V.; Eyermann, C. J.; Chang, C.-H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Li, R.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Hodge, C. N. J. Med. Chem. 1996, 39, 3514-3525.
74. (e) Davis, A. M.; Teague, S. J.; Kleywegt, G. J. Angew. Chem., Int. Ed. 2003, 42, 2718-2736.
75. (f) Loughlin, W. A.; Tyndall, J. D. A.; Glenn, M. P.; Fairlie, D. P. Chem. Rev. 2004, 104, 6085-6117.
76. For an alternative (nonstereoselective) base-induced carbene-type homocoupling to a 2-ene-1,4-diamine, see: Weber, B.; Schwerdtfeger, J.; Fröhlich, R.; Göhrt, A.; Hoppe, D. Synthesis 1999, 1915-1924
77. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
78. Albanese, D.; Landini, D.; Penso, M.; Petricci, S. Tetrahedron 1999, 55, 6387-6394.
79. (a) Kocieński, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933-1940.
80. (b) Hodgson, D. M.; Fleming, M. J.; Stanway, S. J. J. Org. Chem. 2007, 72, 4763-4773.
81. (a) Rao, A. V. R.; Gurjar, M. K.; Pal, S.; Pariza, R. J.; Chorghade, M. S. Tetrahedron Lett. 1995, 36, 2505-2508.
82. (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R.; Pariza, R. J.; Chorghade, M. S. Tetrahedron 1997, 53, 4769-4778.
83. Dondoni, A.; Perrone, D.; Rinaldi, M. J. Org. Chem. 1998, 63, 9252-9264.
84. (a) Zhang, A.; Feng, Y.; Jiang, B. Tetrahedron: Asymmetry 2000, 11, 3123-3130.
85. (b) Zhao, J.; Bao, X.; Liu, X.; Wan, B.; Han, X.; Yang, C.; Hang, J.; Feng, Y.; Jiang, B. Tetrahedron: Asymmetry 2000, 11, 3351-3359.
86. (c) Jiang, B.; Feng, Y.; Hang, J.-F. Tetrahedron: Asymmetry 2001, 12, 2323-2329.
87. (a) Kempf, D. J.; Codacovi, L.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.; Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, D. W. J. Med. Chem. 1993, 36, 320-330.
88. (b) Budt, K.-H.; Peyman, A.; Hansen, J.; Knolle, J.; Meichsner, C.; Paessens, A.; Ruppert, D.; Stowasser, B. Bioorg. Med. Chem. 1995, 3, 559-571.
89. (c) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Mathä, B. J. Med. Chem. 1998, 41, 1581-1597.
90. Moshe, A. Eur. J. Med. Chem. 1981, 16, 199-206.
91. (a) McBriar, M. D.; Guzik, H.; Xu, R.; Paruchova, J.; Li, S.; Palani, A.; Clader, J. W.; Greenlee, W. J.; Hawes, B. E.; Kowalski, T. J.; O'Neill, K.; Spar, B.; Weig, B. J. Med. Chem. 2005, 48, 2274-2277.
92. (b) McBriar, M. D.; Guzik, H.; Shapiro, S.; Paruchova, J.; Xu, R.; Palani, A.; Clader, J. W.; Cox, K.; Greenlee, W. J.; Hawes, B. E.; Kowalski, T. J.; O'Neill, K.; Spar, B. D.; Weig, B.; Weston, D. J.; Farley, C.; Cook, J. J. Med. Chem. 2006, 49, 2294-2310.
93. (c) Kowalski, T. J.; Spar, B. D.; Weig, B.; Farley, C.; Cook, J.; Ghibaudi, L.; Fried, S.; O'Neill, K.; Del Vecchio, R. A.; McBriar, M.; Guzik, H.; Clader, J.; Hawes, B. E.; Hwa J. Eur. J. Pharm. 2006, 535, 182-191.
94. (d) McBriar, M. D.; Guzik, H.; Shapiro, S.; Xu, R.; Paruchova, J.; Clader, J. W.; O'Neill, K.; Hawes, B.; Sorota, S.; Margulis, M.; Tucker, K.; Weston, D. J.; Cox, K. Bioorg. Chem. Med. Lett. 2006, 16, 4262-4265.
95. (a) Rodriquez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J., Jr. J. Med. Chem. 1994, 37, 3389-3399.
96. (b) Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3379-3747.
97. (c) Tchilibon, S.; Joshi, B. V.; Kim, S.-K.; Duong, H. T.; Gao, Z.-G.; Jacobson, K. A. J. Med. Chem. 2005, 48, 1745-1758.
98. (d) Comin, M. J.; Agbaria, R.; Ben-Kasus, T.; Hulaihel, M.; Liao, C.; Sun, G.; Nicklaus, M. C.; Deschamps, J. R.; Parrish, D. A.; Marquez, V. E. J. Am. Chem. Soc. 2007, 129, 6216-6222.
99. Nandanan, E.; Jang, S.-Y.; Moro, S.; Kim, H. O.; Siddiqui, M. O.; Russ, P.; Marquez, V. E.; Busson, R.; Herdewijn, P.; Harden, T. K.; Boyer, J. L.; Jacobson, K. A. J. Med. Chem. 2000, 43, 829-842.
100. (a) Hodgson, D. M.; Chung, Y. K.; Paris, J.-M. J. Am. Chem. Soc. 2004, 126, 8664-8665.
101. (b) Hodgson, D. M.; Chung, Y. K.; Nuzzo, I.; Freixas, G.; Kulikiewicz, K. K.; Cleator, E.; Paris, J.-M. J. Am. Chem. Soc. 2007, 129, 4456-4462.
102. Lapinsky, D. J.; Bergmeier, S. C. Tetrahedron 2002, 58, 7109-7117.
103. (a) Aubrecht, K. B.; Collum, D. B. J. Org. Chem. 1996, 61, 8674-8676.
104. (b) Remenar, J. F.; Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1997, 119, 5567-5572.
105. For an example of the effect of localized high concentrations of organolithium reagents, see: Beak, P.; Musick, T. J.; Chen C. J. Am. Chem. Soc. 1988, 110, 3538-3545.
106. Fraser, R. R.; Mansour, T. S. J. Org. Chem. 1984, 49, 3442-3443.
107. (a) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247-335.
108. (b) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, UK, 1992; Vol. 5, pp 899-970.
109. (c) Oxgaard, J.; Wiest, O. Eur. J. Org. Chem. 2003, 1454-1462.
110. (d) Zuo, G.; Louie, J. Angew. Chem., Int. Ed. 2004, 43, 2277-2279.
111. Kirby, A. J. Stereoelectronic Effects; Oxford University Press: Oxford, UK, 1996; pp 44-46.
112. Bergeron, R. J.; Neims, A. H.; McManis, J. S.; Hawthorne, T. R.; Vinson, J. R. T.; Bortell, R.; Ingeno, M. J. J. Med. Chem. 1988, 31, 1183-1190.
113. Hok, S.; Schore, N. E. J. Org. Chem. 2006, 71, 1736-1738.
114. Friedman, L.; Shechter, H. J. Org. Chem. 1961, 26, 2522-2524.
115. Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Am. Chem. Soc. 1983, 105, 7790-7791.
116. Barrett, P. A.; Caldwell, A. G.; Walls, L. P. J. Chem. Soc. 1961, 2404-2418.