Diastereoselective 1,3-dipolar cycloadditions of chiral derivatives of 2-oxoethanenitrile oxide to noncyclic conjugated symmetrical alkenes

Helvetica Chimica Acta

Volumn 90, Issue 11, 2007, Pages 2116-2131

  Romański, Jan ^a   Jóźwik, Julita ^a   Chapuis, Christian ^b   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITIES; ENANTIOMERIC PURITIES; NITRILE OXIDES; X-RAY CRYSTAL-STRUCTURE ANALYSES;

CONFORMATIONS; CYCLOADDITION; DERIVATIVES; OLEFINS; THERMODYNAMIC STABILITY;

NITROGEN COMPOUNDS;

ALKANE DERIVATIVE; BORANE DERIVATIVE; FUMARIC ACID DERIVATIVE; ISOXAZOLE DERIVATIVE; NITRILE;

ARTICLE; CHEMICAL BOND; CHIRAL CHROMATOGRAPHY; CHIRALITY; CONFORMATION; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR STABILITY; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS; THERMOSTABILITY; X RAY ANALYSIS;

EID: 36549021178     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790219     Document Type: Article

References (98)

1. A. P. Kozikowski, Acc. Chem. Res. 1984, 17, 410;
2. 'Advances in Dipolar Cycloaddition Chemistry', Vol. 1, Ed. D. P. Curran, JAI, Greenwich CT, 1988;
3. 'Organic Synthesis Highlights', Eds. J. Mulzer, W. J. Altenbach, M. Braun, K. Krohn, H. U. Reisig, VCH, Weinheim, 1991;
4. M. Cinquini, F. Cozzi, 'Houben-Weyl', Eds. G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, 1995, Vol. E21c, p. 2953.
5. V. Jäger, H. Grund, V. Buss, W. Schwab, I. Müller, R. Schohe, R. Franz, R. Ehrler, Bull. Soc. Chim. Belg. 1983, 92, 1039;
6. D. P. Curran, J. Am. Chem. Soc. 1983, 105, 5826;
7. A. P. Kozikowski, B. B. Mugrage, J. Chem. Soc., Chem. Commun. 1988, 198;
8. J. de Blas, J. C. Carretero, E. Dominguez, Tetrahedron: Asymmetry 1995, 6, 1035.
9. D. P. Curran, S. A. Scanga, C. J. Fenk, J. Org. Chem. 1984, 49, 3474;
10. V. Jäger, I. Müller, R. Schohe, M. Frey, R. Ehrler, B. Häfele, D. Schröter, Lect. Heterocycl. Chem. 1985, 8, 79.
11. A. A. Hagedorn III, B. J. Miller, J. O. Nagy, Tetrahedron Lett. 1980, 21, 229;
12. S. F. Martin, M. S. Dappen, B. Dupré, C. J. Murphy, J. A. Colapret, J. Org. Chem. 1989, 54, 2209;
13. P. J. Zimmermann, I. Blanarikova, V. Jäger, Angew. Chem., Int. Ed. 2000, 39, 910;
14. C. Ehrhardt, O. Irie, E. Lorthiois, J. Maibaum, N. Ostermann, H. Sellner, WO2006/100036A1 to Novartis AG (2006.09.28), Chem. Abstr. 2006, 145, 32323.
15. P. N. Confalone, G. Pizzolato, D. L. Confalone, M. R. Uskokovic, J. Am. Chem. Soc. 1980, 102, 1954;
16. S. S. Ko, P. N. Confalone, Tetrahedron 1985, 41, 3511;
17. T. Le Gall, J. P. Lellouche, J.-P. Beaucourt, Tetrahedron Lett. 1989, 30, 6521;
18. O. Moriya, H. Takenaka, M. Iyoda, Y. Urata, T. Endo, J. Chem. Soc., Perkin Trans. 1 1994, 413;
19. A. Pal, A. Bhattacharjee, A. Bhattacharjya, A. Patra, Tetrahedron 1999, 55, 4123;
20. A. Pal, A. Bhattacharjee, A. Bhattacharjya, Synthesis 1999, 9, 1569;
21. A. Nivlet, L. Dechoux, J.-P. Martel, G. Proess, D. Mannes, L. Alcaraz, J. J. Harnett, T. Le Gall, C. Mioskowski, Eur. J. Org. Chem. 1999, 12, 3241;
22. R. A. Aungst Jr., C. Chan, R. L. Funk, Org. Lett. 2001, 3, 2611;
23. D. Kim, J. Lee, P. J. Shim, J. I. Lim, H. Jo, S. Kim, J. Org. Chem. 2002, 67, 764;
24. L. D. Fader, E. M. Carreira, Org. Lett. 2004, 6, 2485;
25. S. Ghorai, R. Mukhopadhyay, A. P. Kundu, A. Bhattacharjya, Tetrahedron 2005, 61, 2999;
26. V. Kumar, M. P. Kaushik, Tetrahedron Lett. 2006, 47, 1457.
27. P. C. B. Page, M. Purdle, D. Lathbury, Tetrahedron 1997, 53, 1061;
28. P. A. Wade, H. Le, N. V. Amin, J. Org. Chem. 2002, 67, 2859.
29. D. P. Curran, B. H. Kim, H. P. Piyasena, R. J. Loncharich, K. N. Houk, J. Org. Chem. 1987, 52, 2137;
30. M. T. Rispens, E. Keller, B. de Lange, W. J. Zijlstra, Tetrahedron: Asymmetry 1994, 5, 607.
31. T. Olsson, K. Stern, S. Sundell, J. Org. Chem. 1988, 53, 2468;
32. T. Olsson, K. Stern, G. Westman, S. Sundell, Tetrahedron 1990, 46, 2473.
33. a) D. P. Curran, B. Y. Kim, J. Daughterly, T. A. Heffner, Tetrahedron Lett. 1988, 3555;
34. b) D. P. Curran, T. A. Heffner, J. Org. Chem. 1990, 55, 4585;
35. c) W. Oppolzer, A. J. Kingma, S. K. Pillai, Tetrahedron Lett. 1991, 32, 4893;
36. d) K. S. Kim, B. H. Kim, W. M. Park, S. J. Cho, B. J. Mhin, J. Am. Chem. Soc. 1993, 115, 7472;
37. e) R. H. Wallace, J. Liu, K. K. Zong, A. Eddings, Tetrahedron Lett. 1997, 38, 6791.
38. J. M. J. Tronchet, A. Jotterand, N. Le Hong, M. F. Perret, S. Thorndald-Jaccard, J. Tronchet, J. M. Chalet, M. L. Faivre, C. Hausser, C. Sebastian, Helv. Chim. Acta 1970, 53, 1484;
39. T. Akiyama, K. Okada, S. Ozaki, Tetrahedron Lett. 1992, 33, 5736;
40. A. Pal, A. Bhattacharjya, R. Mukhopadhyay, Tetrahedron Lett. 2000, 41, 10135.
41. U. Sharma, U. Bora, A. Chetia, R. C. Boruah, J. S. Sandhu, Indian J. Chem., Sect. B 2002, 41, 1012.
42. D. P. Curran, K. S. Jeong, T. A. Heffner, J. Rebek Jr., J. Am. Chem. Soc. 1989, 111, 9238;
43. D. P. Curran, M. H. Yoon, Tetrahedron 1997, 53, 1971.
44. C. Kashima, K. Takahashi, I. Fukuchi, K. Fukusaka, Heterocycles 1997, 44, 289;
45. A. Ros, E. Alvarez, H. Dietrich, R. Fernandez, J. M. Lassaletta, Synlett 2005, 19, 2899.
46. J. D. Toker, P. Wentworth, Y. Hu, K. N. Houk, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 3244.
47. K. Rama Rao, N. Banumathi, P. B. Sattur, Tetrahedron Lett. 1990, 31, 3201.
48. Y. Ukaji, K. Sada, K. Inomata, Chem. Lett. 1993, 1847;
49. Y. Yoshida, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 1998, 1023;
50. M. Tsuji, Y. Ukaji, K. Inomata, Chem. Lett. 2002, 1112;
51. M. Serizawa, Y. Ukaji, K. Inomata, Tetrahedron: Asymmetry 2006, 17, 3075.
52. M. Shimizu, Y. Ukaji, K. Inomata, Chem. Lett. 1996, 455;
53. Y. Ukaji, M. Ima, T. Yamada, K. Inomata, Heterocycles 2000, 52, 563;
54. M. P. Sibi, K. Itoh, C. P. Jasperse, J. Am. Chem. Soc. 2004, 126, 5366;
55. Y. Brinkmann, R. J. Madhushaw, R. Jazzar, G. Bernardinelli, E. P. Kündig, Tetrahedron 2007, 63, 8413.
56. A. P. Kozikowski, Y. Kitagawa, J. P. Springer, J. Chem. Soc., Chem. Commun. 1983, 1460;
57. A. P. Kozikowski, S. Goldstein, J. Org. Chem. 1983, 48, 1139;
58. R. H. Jones, G. C. Robinson, E. J. Thomas, Tetrahedron 1984, 40, 177;
59. K. E. Larsen, K. B. G. Torssell, Tetrahedron 1984, 40, 2985;
60. A. P. Kozikowski, X. M. Cheng, J. Chem. Soc., Chem. Commun. 1987, 680;
61. B. H. Kim, Y. J. Chung, G. Keum, J. Kim, K. Kim, Tetrahedron Lett. 1992, 33, 6811.
62. J. Jóźwik, M. Kosior, J. Kiegiel, J. Jurczak, Chirality 2001, 13, 629.
63. I. Kudyba, J. Jóźwik, J. Romański, J. Raczko, J. Jurczak, Tetrahedron: Asymmetry 2005, 16, 2257.
64. J. Romański, J. Jóźwik, C. Chapuis, M. Asztemborska, J. Jurczak, Tetrahedron: Asymmetry 2007, 18, 865.
65. T. Hattori, N. Harada, S. Oi, H. Abe, S. Miyano, Tetrahedron: Asymmetry 1995, 6, 1043;
66. N. Harada, T. Soutome, S. Murai, H. Uda, Tetrahedron: Asymmetry 1993, 4, 1755.
67. T. Bauer, C. Chapuis, J. Kiegiel, J. W. Krajewski, K. Piechota, Z. Urbanczyk-Lipkowska, J. Jurczak, Helv. Chim. Acta 1996, 79, 1059.
68. C. Chapuis, J.-Y. De Saint Laumer, M. Marty, Helv. Chim. Acta 1997, 80, 146.
69. J. Kalvoda, H. Kaufmann, J. Chem. Soc., Chem. Commun. 1976, 209.
70. T. Shimizu, Y. Hayshi, H. Shibafuchi, K. Teramura, Bull. Chem. Soc. Jpn. 1986, 59, 2827.
71. W. Kroszczynski, E. Olszewska, P. Salanski, J. Jurczak, Helv. Chim. Acta 2004, 87, 1488.
72. a) A. Chojnacka, A. Piatek, C. Chapuis, J. Jurczak, Tetrahedron: Asymmetry 2006, 17, 822;
73. b) A. Piatek, C. Chapuis, J. Jurczak, J. Phys. Org. Chem. 2003, 16, 700;
74. c) T. Bauer, C. Chapuis, A. Kucharska, P. Rzepecki, J. Jurczak, Helv. Chim. Acta 1998, 81, 324.
75. Gaussian 98, Revision A.7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi. V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1998;
76. J. A. R. Luft, K. Meleson, K. N. Houk, Org. Lett. 2007, 9, 555.
77. R. Sustmann, H. Trill, Angew. Chem., Int. Ed. 1972, 11, 838.
78. A. Corsaro, U. Chiacchio, V. Pistarà, A. Rescifina, G. Buemi, G. Romeo, J. Chem. Soc., Perkin Trans. 2 2000, 1761.
79. T. Bauer, C. Chapuis, A. Jezewski, J. Kozak, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1391.
80. B. H. Kim, D. P. Curran, Tetrahedron 1993, 49, 293.
81. A. M. Piatek, A. Chojnacka, C. Chapuis, J. Jurczak, Helv. Chim. Acta 2005, 88, 2441.
82. W. Oppolzer, C. Chapuis, D. Dupuis, M. Guo, Helv. Chim. Acta 1985, 68, 2100.
83. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209;
84. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 221.
85. A. Kucharska, R. Gorczynska, C. Chapuis, J. Jurczak, Chirality 2001, 13, 631.
86. T. Rispens, J. B. F. N. Engberts, J. Phys. Org. Chem. 2005, 18, 908;
87. R. Huisgen, G. Mlostón, E. Langhals, J. Am. Chem. Soc. 1986, 108, 6401.
88. J. Raczko, M. Achmatowicz, A. Jezewski, C. Chapuis, Z. Urbanczyk-Lipkowska, J. Jurczak, Helv. Chim. Acta 1998, 81, 1264.
89. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171.NET) (compiled Oct 25 2005,08:50:05).
90. CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta.
91. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
92. G. M. Sheldrick, SHELXL93, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, 1993.
93. 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer, Dordrecht, 1992, Vol. C.
94. H. D. Flack, Acta Crystallogr., Sect. C 1983, 39, 876;
95. H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect. A 1999, 55, 908;
96. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
97. D. Cremer, J. A. Pople, J. Am. Chem. Soc. 1975, 97, 1354.
98. www.hyper.com/support/download/Macros/macros_index.html.