Use of chiral Ti(IV) complexes in the cycloaddition of C,N- diphenylnitrone to tert-butyl vinyl ether

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1757-1765

  Bayón, Pau ^a   De March, Pedro ^a   Espinosa, Mercè ^a   Figueredo, Marta ^a   Font, Josep ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; NITRONE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034608075     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00115-4     Document Type: Article

References (30)

1. (a) Tufariello, J. J. 1,3-Dipolar Cycloaddition Chemistry; John Wiley and Sons: New York, 1984; Vol. 2, Chapter 9;
2. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH Verlagsgesellschaft: Weinheim, 1988.
3. Reviews on asymmetric cycloadditions of nitrones: (a) Frederickson, M. Tetrahedron 1997, 53, 403-425;
4. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909.
5. (a) Sanchez-Blanco, A. I.; Gothelf, K. V.; Jørgensen, K. A. Tetrahedron Lett. 1997, 38, 7923-7926;
6. (b) Gilberstone, S. R.; Lopez, O. D. J. Am. Chem. Soc. 1997, 119, 3399-3400;
7. (c) Kanemasa, S.; Oderaotoshi, Y.; Tanaka, J.; Wada, E. J. Am. Chem. Soc. 1998, 120, 12 355-12 356;
8. (d) Minakata, S.; Ezoe, T.; Nakamura, K.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 5205-5208;
9. (e) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840-5841;
10. (f) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023;
11. (g) Desimoni, G.; Faita, G.; Mortoni, A.; Righetti, P. Tetrahedron Lett. 1999, 40, 2001-2004.
12. (a) Seerden, J.-P. G.; Boeren, M. M. M.; Scheeren, H. W. Tetrahedron 1997, 53, 11 843-11 852;
13. (b) Meske, M. J. Prakt. Chem. 1997, 426-433;
14. (c) Hori, K.; Ito, J.; Ohta, T.; Furukawa, I. Tetrahedron 1998, 54, 12737-12744;
15. (d) Simonsen, K. B.; Jørgensen, K. A.; Hu, Q.-S.; Pu, L. Chem. Commun. 1999, 811-812;
16. (e) Jensen, K. B.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 2353-2360;
17. (f) Ohtake, H.; Imada, Y.; Murahashi, S.-I. J. Org. Chem. 1999, 64, 3790-3791.
18. Bayón, P.; de March, P.; Figueredo, M.; Font, J. Tetrahedron 1998, 54, 15 691-15 700.
19. Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Acta Chem. Scand. 1997, 50, 1234-1235.
20. Although some titanium complexes of 1,2-diolates present dimeric structures in solution: Duthaler, R. O.; Hafner, A. Chem Rev. 1992, 92, 807-832.
21. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itho, K. Organometallics 1991, 10, 500-508.
22. Ellis, W. W.; Gavrilova, A.; Liable-Sands, L.; Rheingold, A. L.; Bosnich, B. Organometallics 1999, 18, 332-338.
23. Simonsen, K. B.; Bayón, P.; Hazell, R. H.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 1999, 121, 3845-3853.
24. Wheeler, O. H.; Gore, P. H. J. Am. Chem. Soc. 1956, 78, 3363-3366.
25. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2786.
26. De March, P.; Figueredo, M.; Font, J.; Medrano, J. Tetrahedron 1999, 55, 7907-7914.
27. Beck, A. K.; Bastani, B.; Plattner, D. A.; Petter, W.; Seebach, D.; Braunschweiger, H.; Gysi, P.; La Vecchia, L. Chimia 1991, 45, 238-244.
28. Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149-1151.
29. Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691.
30. Jensen, K. B.; Gothelf, K. V.; Jørgensen, K. A. Helv. Chim. Acta 1997, 80, 2039-2045.