1,4-Asymmetric induction in methoxyselenenylation of double bonds at the nitrogen side of chiral perhydro-1,3-benzoxazines promoted by nonbonded Se⋯N interactions

Journal of Organic Chemistry

Volumn 71, Issue 14, 2006, Pages 5388-5391

  Pedrosa, Rafael ^a   Andrés, Celia ^a   Mendiguchía, Pilar ^a   Nieto, Javier ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLAMINE SYSTEMS; BENZENESELENENYL CHLORIDE; CINNAMYLAMINES; DIASTEREOSELECTIVE;

ALCOHOLS; AROMATIC COMPOUNDS; CHEMICAL BONDS; REACTION KINETICS; SELENIUM; THERMAL EFFECTS;

NITROGEN COMPOUNDS;

2 VINYLPERHYDRO 1,3 BENZOXAZINE; ACETALDEHYDE; AMINE; BENZALDEHYDE; BENZOXAZINE DERIVATIVE; CINNAMALDEHYDE; DICHLOROMETHANE; GLUTATHIONE PEROXIDASE; METHANOL; NITROGEN; ORGANOSELENIUM DERIVATIVE; OXAZINE DERIVATIVE; PERHYDRO 1,3 BENZOXAZINE; SELENIUM; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; COLUMN CHROMATOGRAPHY; CYCLIZATION; DIASTEREOISOMER; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

BENZOXAZINES; MOLECULAR CONFORMATION; NITROGEN; ORGANOSELENIUM COMPOUNDS; SELENIUM; STEREOISOMERISM;

EID: 33745685990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060566r     Document Type: Article

References (44)

1. (a) Burling, F. T.; Goldstein, M. B. J. Am. Chem. Soc. 1992, 114, 2313.
2. (b) Goldstein, M. B.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265.
3. (c) Goldstein, F.; Takusagawa, Y.; Berman, H. M.; Srivastava, P. C.; Robins, R. K. J. Am. Chem. Soc. 1985, 107, 1394.
4. (a) Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2002, 124, 12104.
5. (b) Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. Am. Chem. Soc. 2001, 123, 839.
6. (c) Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125.
7. (d) Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347.
8. (e) Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1992, 1165.
9. (f) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557.
10. (a) Kandasamy, K.; Kumar, S.; Singh, H. B.; Butcher, R. J.; Holman, K. T. Eur. J. Inorg. Chem. 2004, 1014 and references therein.
11. (b) Mugesh, G.; Singh, H. B.; Butcher, R. Tetrahedron: Asymmetry 1999, 10, 237.
12. (c) Iwaoka, M.; Tomoda, S. J. Org. Chem. 1995, 60, 5299.
13. (a) Spichty, M.; Fragale, G.; Wirth, T. J. Am. Chem. Soc. 2000, 122, 10914.
14. (b) Wang, X.; Houk, K. N.; Spichty, M.; Wirth, T. J. Am. Chem. Soc. 1999, 121, 8567.
15. (c) Wirth, T.; Fragale, G.; Spichty, M. J. Am. Chem. Soc. 1998, 120, 3376.
16. (a) Back, T. G.; Moussa, Z.; Parvez, M. J. Org. Chem. 2002, 67, 499.
17. (b) Uehlin, L.; Fragale, G.; Wirth, T. Chem.-Eur. J. 2002, 8, 1125.
18. (c) Tiecco, M.; Testaferri, L.; Bagnoli, L.; Marini, F.; Temperini, A.; Tomassini, C.; Santi, C. Tetrahedron Lett. 2000, 41, 3241.
19. (d) Fragale, G.; Neuburger, M.; Wirth, T. Chem. Commun. 1998, 1867.
20. (e) Fujita, K.; Murata, K.; Iwaoka, M.; Shuji, T. Tetrahedron 1997, 53, 2029.
21. (a) Khokhar, S. S.; Wirth, T. Angew. Chem., Int. Ed. 2004, 43, 631.
22. (b) Khokhar, S. S.; Wirth, T. Eur. J. Org. Chem. 2004, 4567.
23. (a) Mugesh, G.; Panda, A.; Singh, H. B.; Butcher, R. J. Chem.-Eur. J. 1999, 5, 1411.
24. (b) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1996, 118, 8077. See also ref 3b.
25. (a) Komatsu, T.; Iwaoka, M.; Tomoda, S. Chem. Commun. 1999. 205.
26. (b) Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomoda, S. J. Am. Chem. Soc. 2004, 126, 5309.
27. (c) Barton, D. H. R.; Hall, H. B.; Lin, Z.; Parekh, S. I.; Reibenspies, J. J. Am. Chem. Soc. 1993, 115, 5056.
28. (a) Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomoda, S. J. Am. Chem. Soc. 2002, 124, 1902.
29. (b) Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomoda, S. J. Org. Chem. 2005, 70, 321.
30. Pedrosa, R.; Andrés, C.; Arias, R.; Mendiguchía, P.; Nieto, J. J. Org. Chem. 2006, 71, 2424.
31. (a) Cooper, M. A.; Ward, D. Tetrahedron 2004, 60, 7963.
32. (b) Aprile, C.; Gruttadauria, M.; Amato, M.- E.; D'Anna, F.; Lo Meo, P.; Riela, S.; Noto, R. Tetrahedron 2003, 59, 2241.
33. (c) Kim, K. S.; Ahn, K. O.; Park, J., II. Bull. Korean Chem. Soc. 1997, 18, 800.
34. (d) Kim, K. S.; Park, H. B.; Kim, J. Y.; Ahn, Y. H.; Jeong, H. I. Tetrahedron Lett. 1996, 37, 1249.
35. (e) Cooper, M. A.; Ward, D. Tetrahedron Lett. 1995, 36, 2327.
36. (f) Haughan, A. F.; Knight, J. R.; Sweeney, J. B. Tetrahedron Lett. 1994, 35, 1781.
37. (g) Liotta, D.; Zima, G.; Saindane, M. J. Org. Chem. 1982, 47, 1258.
38. For different examples of regio- and diastereoselective addition reactions to chiral allylic amines, see: (a) Aggarwal, V. K.; Fang, G. Y.; Meek, G. Org. Lett. 2003, 5, 4417.
39. (b) Lai, J.-Y.; Shi, X.-X.; Gong, Y.-S.; Dai, L.-X. J. Org. Chem. 1993, 58, 4775.
40. (c) Lai, J.-Y.; Wang, F.-S.; Guo, G.-Z.; Dai, L.-X. J. Org. Chem. 1993, 58, 6944.
41. Pedrosa, R.; Andrés, C.; Nieto, J. J. Org. Chem. 2002, 67, 782.
42. The use of different electrophilic reagents, such as PhSeBr or PhSeOTf, did not improve the results obtained with PhSeCl.
43. Crystallographic data can be obtained from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK. E-mail: deposit@ccdc.cam.ac. uk
44. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; p 753.