Planar-chiral cyclopalladated ferrocenyl amines and imines as enantioselective catalysts for allylic imidate rearrangements

Tetrahedron Asymmetry

Volumn 9, Issue 18, 1998, Pages 3213-3222

  Cohen, Frederick ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; FERROCENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032544783     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00341-3     Document Type: Article

References (21)

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2. 2. Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837.
3. 3. For notable recent contributions, see: (a) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790.
4. (b) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.
5. 4. For brief reviews of allylic imidate rearrangements, see: (a) Jørgensen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689.
6. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
7. (c) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
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11. (b) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
12. 8. For a recent review of the synthesis of enantioenriched chiral ferrocenes, see: Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, pp. 189-235.
13. 9. (a) Sokolov, V. I.; Troitskaya, L. L.; Reutov, J. J. Organomet. Chem. 1977, 133, C28.
14. (b) Sokolov, V. I.; Troitskaya, L. L.; Reutov, J. Dokl. Akad. Nauk SSSR 1977, 236, 371.
15. 10. For reviews of cyclopalladation, see: (a) Canty, A. J. In Comprehensive Organometallic Chemistry II 1995, 9, 242-248.
16. (b) Rayabov, A. D. Synthesis 1985, 233.
17. 11. Zhao, G.; Xue, F. Z. Z.-Y.; Mak, T. C. W. Organometallics 1997, 19, 4023.
18. 12. For example: Blanco, J.; Gayoso, E.; Vila, J. M.; Gayoso, M.; Maichle-Mossmer, C.; Strahle, J. Z. Naturforsch. 1993, 48b, 906.
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20. 14. Competing elimination reactions have also plagued another group's work in this area: Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
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