Entropy-controlled diastereoselectivity in the photocyclization of rigid derivatives of o-allylaniline

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7915-7918

  Benali, Otman ^a   Miranda, Miguel A ^a   Tormos, Rosa ^a   Gil, Salvador ^b  

^a INSTITUTO DE TECNOLOGÍA QUÍMICA   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOCYCLIZATION;

ELECTRON TRANSITIONS; ENTROPY; ORGANIC COMPOUNDS; PHOTOLYSIS;

DERIVATIVES;

2 ALLYLANILINE DERIVATIVE; 7 (2 CINNAMYL) 2 METHYLINDOLINE; 8 ALLYL 2 PHENYL 1,2,3,4 TETRAHYDROQUINOLINE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ELECTRON TRANSPORT; ENTROPY; FLUORESCENCE SPECTROSCOPY; INFRARED SPECTROSCOPY; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE SENSITIVITY;

EID: 0036827562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020355w     Document Type: Article

References (22)

1. Nógrádi, M. Stereoselective Synthesis: A Practical Approach, 2nd Ed.; Wiley-VCH: Weinheim, Germany, 1994.
2. Gawley, R. E.; Aubè, J. Principles of Asymmetric Synthesis; Pergamon: Oxford, UK, 1996.
3. Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis: Graphical Abstracts and Experimental Methods; Kodansha/Gordon and Breach: Tokyo/Amsterdam, 1998.
4. Rau, H. Chem. Rev. 1983, 83, 535 -547.
5. Inoue, Y. Chem. Rev. 1992, 92, 741-770.
6. (a) Inoue, Y.; Wada, T.; Asaoka, S.; Sato, H.; Pete, J. P. Chem. Commun. 1999, 251-259.
7. (b) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486-8498.
8. (a) Koch, H.; Runsink, J.; Scharf, H.-D.; Leismann, H. Chem. Ber. 1985, 118, 1485-1503.
9. (b) Buschmann, H.; Scharf, H.-D.; Hoffman, N.; Plath, M. W.; Runsink, J. J. Am. Chem. Soc. 1989, 111, 5367-5373.
10. (c) Koch, H.; Runsink, J.; Scharf, H.-D. Tetrahedron Lett. 1983, 24, 3217-3320.
11. (a) Paillous, N.; Lattes, A. Tetrahedron 1971, 52, 4945-4948.
12. (b) Koch-Pomeranz, U.; Hansen, H. J. Helv. Chim. Acta 1975, 58, 178-182.
13. (c) Koch-Pomeranz, U.; Hansen, H. J. Helv. Chim. Acta 1977, 60, 768-797.
14. (d) Jolidon, S.; Hansen, H. J. Helv. Chim. Acta 1979, 62, 2581-2611.
15. (e) Scholl, B.; Hansen, H. J. Helv. Chim. Acta 1980, 63, 1823-1832.
16. (f) Scholl, B.; Hansen, H. J. Chimia 1981, 35, 49-51.
17. (g) Scholl, B.; Jolidon, S.; Hansen, H. J. Helv. Chim. Acta 1986, 69, 184-194.
18. Lewis, F. D.; Wagner-Brennan, J. M.; Miller, A. M. Can. J. Chem. 1999, 77, 595-604.
19. Abonia, R.; Albornoz, A.; Insausty, B.; Quiroga, J.; Meier, H.; Hormaza, A.; Nogueras, M.; Sánchez, A.; Cobo, J.; Low, J. N. Tetrahedron 2001, 57, 4933-4938.
20. Moody, C. J.; Pitts, M. R. Synlett 1998, 1029-1030.
21. Heany, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1973, 5, 499-500.
22. Hurd, C. D.; Jenkins, W. W. J. Org. Chem. 1957, 22, 1418- 1423.