Entrapment and kinetic resolution of stabilized axial and equatorial conformers of spiro-β-lactams

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 5999-6006

  Anand, Naveen ^a,e   Shah, Bhahwal A ^a   Kapoor, Munish ^a   Parshad, Rajinder ^a   Sharma, Rattan L ^b   Hundal, Maninder S ^c   Pannu, Ajay P S ^c   Bharatam, Prasad V ^c,d   Taneja, Subhash C ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b UNIVERSITY OF JAMMU   (India)

^c GURU NANAK DEV UNIVERSITY   (India)

^d NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^e Govt College for Women   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTION; CYCLOHEXANONES; EQUATORIAL CONFORMERS; FACILE SYNTHESIS; KINETIC RESOLUTION; QUANTUM CHEMICAL CALCULATIONS; RACEMIC SUBSTRATES; SCHIFF BASIS; SOLID SUPPORTS;

AMIDES; CHLORINE COMPOUNDS; CYCLOADDITION; ENANTIOSELECTIVITY; FUNCTIONAL GROUPS; QUANTUM CHEMISTRY; SYNTHESIS (CHEMICAL);

KINETICS;

ACETOXYACETYL CHLORIDE; BETA LACTAM; CHLORIDE; CYCLOHEXANONE IMINE; SCHIFF BASE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; CYCLOADDITION; ENANTIOSELECTIVITY; QUANTUM CHEMISTRY; RACEMIZATION; REACTION TIME; SOLID; SYNTHESIS;

BETA-LACTAMS; IMINES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; SCHIFF BASES; STEREOISOMERISM;

EID: 79961076430     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200363x     Document Type: Article

References (66)

1. Alcaide, B.; Almendros, P.; Campo, T. M.; Acebes, R. R. Tetrahedron Lett. 2004, 45, 6429-31
2. Setti, E. L.; Micetich, R. G. Curr. Med. Chem. 1998, 5, 101-14
3. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
4. Page, M. I.; Laws, A. P. Tetrahedron 2000, 56, 5631-38
5. Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LaPlante, S. R.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deziel, R. J. Am. Chem. Soc. 1999, 121, 2965-73
6. Vaccaro, W. D.; Davis, H. R. Bioorg. Med. Chem. Lett. 1998, 8, 313-18 For reviews, see: Alcaide, B.; Almendros, P. Synlett 2002, 381-93
7. Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226-40
8. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813-27
9. Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377-87
10. Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755-1802
11. Banik, B. K.; Samajdar, S.; Becker, F. F. Mol. Med. Rep. 2010, 3, 319-21
12. O'Boyle, N. M.; Greene, L. M.; Bergin, O.; Fichet, J. B.; McCabe, T.; Lloyd, D. G.; Zisterer, D. M.; Meegan, M. J. Bioorg. Med. Chem. 2011, 19, 2306-25
13. He, P.; Nie, Y. B.; Wu, J.; Ding, M. W. Org. Biomol. Chem. 2011, 9, 1429-36
14. Li, X.; Yin, Q.; Jiao, L.; Qin, Z.; Feng, J.; Chen, H.; Zhang, J.; Meng, M. Carbohydr. Res. 2011, 346, 401-09
15. Chen, H.; Zhao, J.; Li, Y.; Shen, F.; Li, X.; Yin, Q.; Qin, Z.; Yan, X.; Wang, Y.; Zhang, P.; Zhang, J. Bioorg. Med. Chem. Lett. 2011, 21, 574-76
16. Ibrahim, Y. A.; Al-Azemi, T. F.; Abd El-Halim, M. D. J. Org. Chem. 2010, 75, 4508-13
17. Feroci, M.; Chiarotto, I.; Orsini, M.; Inesi, A. Chem. Commun. 2010, 46, 4121-23
18. Banik, B. K.; Banik, I.; Becker, F. F. Eur. J. Med. Chem. 2010, 45, 846-48
19. Ibrahim, Y. A.; Al-Azemi, T. F.; Abd El-Halim, M. D.; John, E. J. Org. Chem. 2009, 74, 4305-10
20. Burés, J.; Martín, M.; Urpí, F.; Vilarrasa, J. J. Org. Chem. 2009, 74, 2203-6
21. Zhang, Y. R.; He, L.; Wu, X.; Shao, P. L.; Ye, S. Org. Lett. 2008, 10, 277-80
22. Charafeddine, A.; Dayoub, W.; Chapuis, H.; Strazewski, P. Chemistry 2007, 13, 5566-84
23. Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6080
24. Alonso, E.; Lopez-Ortiz, F.; del Pozo, C.; Macias, A.; Gonzalez, J. J. Org. Chem. 2001, 66, 6333-38
25. Alonso, E.; del Pozo, C.; Gonzalez, J. Synlett 2002, 69-72
26. Kambara, T.; Tomioka, K. J. Org. Chem. 1999, 64, 9282-85
27. Khasanov, A. B.; Ramirez-Weinhouse, M. M.; Webb, T. R.; Thiruvazhi, M. J. Org. Chem. 2004, 69, 5766-69
28. Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, 6, 2507-10
29. Macias, A.; Alonso, E.; del Pozo, C.; Venturini, A.; Gonzalez, J. J. Org. Chem. 2004, 69, 7004-12
30. Arora, R.; Venugopalan, P.; Bari, S. S. J. Chem. Sci. 2010, 122, 125
31. Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995.
32. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; JohnWiley & Sons: New York, 1994.
33. Han, S.; Yoo, H. S.; Kim, S. K. J. Phys. Chem. A. 2010, 114, 10005-10
34. Gill, G.; Pawar, D. M.; Noe, E. A. J. Org. Chem. 2005, 70, 10726-31
35. Dugar, S.; Clader, J. W.; Chan, T.-M.; Davis, H., Jr. J. Med. Chem. 1995, 38, 4875-77
36. Burnett, D. A.; Caplen, M. A.; Davis, H. R., Jr.; Burrier, R. E.; Clader, L. W. J. Med. Chem. 1994, 37, 1733-36
37. Wu, G.; Tormos, W. J. Org. Chem. 1997, 62, 6412-14
38. Cremonesi, G.; Croce, P. D.; Fontana, F.; Rosa, C. L. J. Org. Chem. 2010, 75, 2010-17
39. Moriconi, E. J.; Kelly, J. F. J. Am. Chem. Soc. 1966, 88, 365-66
40. Moriconi, E. J.; Kelly, J. F. J. Org. Chem. 1968, 33, 3036-46
41. Moriconi, E. J.; Kelly, J. F. Tetrahedron Lett. 1968, 24, 1435-39
42. Manhas, M. S.; Chib, J. S.; Chiang, Y. H.; Bose, A. K. Tetrahedron Lett. 1969, 25, 4421-26
43. Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51-123
44. Itoh, T.; Kuroda, K.; Tomosada, M.; Takagi, Y. J. Org. Chem. 1991, 56, 797-804
45. Taskinen, E. Struct. Chem. 1998, 9, 411-18
46. Alan, R.; Potts, A. R.; Baer, T. J. Mol. Struct.: THEOCHEM 1997, 419, 11-18
47. Lightner, D. A.; Crist, B. V. Appl. Spectrosc. 1979, 33, 307-10
48. Cossio, F. P.; Arrieta, A.; Sierra, M. A. Acc. Chem. Res. 2008, 41, 925-36 and the references cited therein. Liang, Y.; Jiao, L.; Zhang, S.; Yu, Z. X.; Xu, J. J. Am. Chem. Soc. 2009, 131, 1542-49
49. Pacansky, J.; Chang, J. S.; Brown, D. W.; Schwarz, W. J. Org. Chem. 1982, 47, 2233-34
50. Moore, H. W.; Hughes, G.; Srinivasachar, K.; Fernandez, M.; Nguyen, N. V.; Schoon, D.; Tranne, A. J. Org. Chem. 1985, 50, 4231-38
51. Lynch, J. E.; Riseman, S. M.; Laswell, W. L.; Tschaen, D. M.; Volante, R. P.; Smith, G. B.; Shinkai, I. J. Org. Chem. 1989, 54, 3792-96
52. Venturini, A.; Gonzalez, J. J. Org. Chem. 2002, 67, 9089-92
53. Bharatam, P. V.; Kumar, R. S.; Mahajan, M. P. Org. Lett. 2000, 2, 2725-27
54. Qi, H.; Li, X.; Xu, J. Org. Biomol. Chem. 2011, 9, 2702-14
55. Assfeld, X.; Ruiz-lopez, M. F.; Gonzalez, J.; Lopez, R.; Sordo, J. A.; Sordo, T. L. J. Comput. Chem. 1994, 15, 479
56. Compomanes, P.; Menendez, M. I.; Sordo, T. L. J. Phys. Chem. A 2005, 109, 11022-26
57. Cieplack, A. S. J. Am. Chem. Soc. 1981, 103, 4540-52
58. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115
59. Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
60. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
61. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
62. Bartolotti, L. J.; Fluchick, K. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7, p 187.
63. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
64. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
65. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.