Asymmetric induction during photocyclization of chiral and achiral α-oxoamides within achiral zeolites

Organic and Biomolecular Chemistry

Volumn 4, Issue 24, 2006, Pages 4533-4542

  Natarajan, Arunkumar ^a   Ramamurthy, V ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; MATHEMATICAL MODELS; PHOTOCHEMICAL REACTIONS; REACTION KINETICS;

ACHIRAL ZEOLITES; ASYMMETRIC INDUCTION; OXOAMIDES;

ZEOLITES;

EID: 33751582931     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b611387g     Document Type: Article

References (56)

1. A. Bauer F. Westkaemper S. Grimme T. Bach Nature 2005 436 1139
2. B. Grosch and T. Bach, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
3. S. R. L. Everitt and Y. Inoue, in Molecular and Supramolecular Photochemistry, ed., V. Ramamurthy, and, K. Schanze, Marcel Dekker, Inc., New York, 1999
4. T. Wada and Y. Inoue, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
5. N. Hoffmann and J.-P. Pete, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
6. H. Buschmann H.-D. Scharf N. Hoffmann P. Esser Angew. Chem., Int. Ed. Engl. 1991 30 477
7. J. R. Scheffer W. Xia Top. Curr. Chem. 2005 254 233
8. J. R. Scheffer, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
9. K. Tanaka and F. Toda, in Organic Photoreactions in the Solid State, ed., F. Toda, Kluwer Academic Publishers, New York, 2002
10. F. Toda, K. Tanaka and H. Miyamoto, in Understanding and Manipulating Excited-State Processes, ed., V. Ramamurthy, and, K. S. Schanze, Marcel Dekker, Inc., New York, 2001
11. V. P. Rao N. J. Turro Tetrahedron Lett. 1989 30 4641
12. A. Joy V. Ramamurthy Chem.-Eur. J. 2000 6 1287
13. J. Sivaguru A. Natarajan L. S. Kaanumalle J. Shailaja S. Uppili A. Joy V. Ramamurthy Acc. Chem. Res. 2003 36 509
14. V. Ramamurthy, A. Natarajan, L. S. Kaanumalle, S. Karthikeyan, J. Sivaguru, J. Shailaja and A. Joy, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
15. G. S. Hammond R. S. Cole J. Am. Chem. Soc. 1965 87 3256
16. H. Kagan A. Moradpour J. F. Nicoud G. Balavoine R. H. Martin J. P. Cosyn Tetrahedron Lett. 1971 27 2479
17. G. Balavoine A. Moradpour H. B. Kagan J. Am. Chem. Soc. 1974 96 5152
18. W. J. Bernstein M. Calvin O. Buchardt Tetrahedron Lett. 1972 22 2195
19. A. Elgavi B. S. Green G. M. J. Schmidt J. Am. Chem. Soc. 1973 95 2058
20. K. Penzien G. M. J. Schmidt Angew. Chem., Int. Ed. Engl. 1969 8 608
21. J.-P. Pete, in Advances in Photochemistry, ed., D. C. Neckers, D. H. Volman, and, G. Von Bunan, Wiley, New York, 1996
22. L. Addadi M. Lahav Pure Appl. Chem. 1979 51 1269
23. M. Sakamoto, in Chiral Photochemistry, ed., Y. Inoue, and, V. Ramamurthy, Marcel Dekker, Inc., New York, 2004
24. J. N. Gamlin R. Jones M. Leibovitch B. Patrick J. R. Scheffer J. Trotter Acc. Chem. Res. 1996 29 203
25. Y. Weisinger-Lewin M. Vaida R. Popovitz-Biro H. C. Chang F. Mannig F. Frolow M. Lahav L. Leiserowitz Tetrahedron 1987 43 1449
26. S. Koodanjeri A. Joy V. Ramamurthy Tetrahedron 2000 56 7003
27. S. Koodanjeri V. Ramamurthy Tetrahedron Lett. 2002 43 9229
28. J. Shailaja S. Karthikeyan V. Ramamurthy Tetrahedron Lett. 2002 43 9335
29. N. Levi-Menzi M. Zandomeneghi J. Am. Chem. Soc. 1992 114 9300
30. T. Wada M. Nishijima T. Fujisawa N. Sugahara T. Mori A. Nakamura Y. Inoue J. Am. Chem. Soc. 2003 125 7492
31. T. Wada N. Sugahara M. Kawano Y. Inoue Chem. Lett. 2000 1174
32. M. Zandomeneghi J. Am. Chem. Soc. 1991 113 7774
33. A. Joy L. S. Kaanumalle V. Ramamurthy Org. Biomol. Chem. 2005 3 3045
34. J. Shailaja L. S. Kaanumalle K. Sivasubramanian A. Natarajan K. Ponchot A. R. Pradhan V. Ramamurthy Org. Biomol. Chem. 2006 4 1561
35. A. Natarajan V. Ramamurthy J. T. Mague Mol. Cryst. Liq. Cryst. 2006 456 71
36. J. Sivaguru R. B. Sunoj T. Wada Y. Origane Y. Inoue V. Ramamurthy J. Org. Chem. 2004 69 5528
37. J. Sivaguru R. B. Sunoj T. Wada Y. Origane Y. Inoue V. Ramamurthy J. Org. Chem. 2004 69 6533
38. L. S. Kaanumalle J. Sivaguru R. B. Sunoj P. H. Lakshminarasimhan J. Chandrasekhar V. Ramamurthy J. Org. Chem. 2002 67 8711
39. A. Natarajan A. Joy L. S. Kaanumalle J. R. Scheffer V. Ramamurthy J. Org. Chem. 2002 67 8339
40. J. Sivaguru T. Wada Y. Origane Y. Inoue V. Ramamurthy Photochem. Photobiol. Sci. 2005 4 119
41. L. S. Kaanumalle J. Sivaguru N. Arunkumar S. Karthikeyan V. Ramamurthy Chem. Commun. 2003 116
42. A. Natarajan K. Wang V. Ramamurthy J. R. Scheffer B. Patrick Org. Lett. 2002 4 1443
43. H. Aoyama M. Sakamoto Y. Omote J. Chem. Soc., Perkin Trans. 1 1981 1357
44. H. Aoyama M. Hasegawa M. Watabe H. Shiraishi Y. Omote J. Org. Chem. 1978 43 419
45. H. Aoyama M. Sakamoto K. Kuwabara K. Yoshida Y. Omote J. Am. Chem. Soc. 1983 105 1958
46. C. A. Chesta D. G. Whitten J. Am. Chem. Soc. 1992 114 2188
47. R. Wang C. Chen E. Duesler P. S. Mariano J. Org. Chem. 2004 69 1215
48. A. Natarajan J. T. Mague V. Ramamurthy J. Am. Chem. Soc. 2005 127 3568
49. A. Joy S. Uppili M. R. Netherton J. R. Scheffer V. Ramamurthy J. Am. Chem. Soc. 2000 122 728
50. S. Uppili V. Ramamurthy Org. Lett. 2002 4 87
51. Y. Inoue T. Yokoyama N. Yamasaki A. Tai Nature 1989 341 225
52. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. Montgomery, J. A. T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, ' Gaussian 98, Revision A.11 ', Pittsburgh, 1998
53. R. C. Dunbar J. Phys. Chem. A 2000 104 8067
54. R. A. Jockusch A. S. Lemoff E. R. Williams J. Phys. Chem. A 2001 105 10929
55. R. A. Jockusch W. D. Price E. R. Williams J. Phys. Chem. A 1999 103 9266
56. S. Hoyau G. Ohanessian Chem.-Eur. J. 1998 4 1561