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Volumn 44, Issue 12, 2005, Pages 1865-1869

Oxazoline-mediated interannular cyclopalladation of ferrocene: Chiral palladium(II) catalysts for the enantioselective aza-Claisen rearrangement

Author keywords

Allylic compounds; Asymmetric catalysis; Metalation; Metallocenes; Palladium

Indexed keywords

CATALYSIS; CATALYSTS;

EID: 17044397325     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462434     Document Type: Article
Times cited : (141)

References (62)
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    • A few examples of interannular lithiation of ferrocenes can be found in the literature, see: a) G. Iftime, C. Moreau-Bossuet, E. Manoury, G. G. A. Balavoine, Chem. Commun. 1996, 527-528; b) G. Iftime, J.-C. Daran, E. Manoury, G. G. A. Balavoine, Organometallics 1996, 15, 4808-4815; c) M. Tsukazaki, M. Tinkl, A. Roglans, B. J. Chapell, N, J. Taylor, V. Snieckus, J. Am. Chem. Soc. 1996, 118, 685-686.
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    • A few examples of interannular lithiation of ferrocenes can be found in the literature, see: a) G. Iftime, C. Moreau-Bossuet, E. Manoury, G. G. A. Balavoine, Chem. Commun. 1996, 527-528; b) G. Iftime, J.-C. Daran, E. Manoury, G. G. A. Balavoine, Organometallics 1996, 15, 4808-4815; c) M. Tsukazaki, M. Tinkl, A. Roglans, B. J. Chapell, N, J. Taylor, V. Snieckus, J. Am. Chem. Soc. 1996, 118, 685-686.
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    • A few examples of interannular lithiation of ferrocenes can be found in the literature, see: a) G. Iftime, C. Moreau-Bossuet, E. Manoury, G. G. A. Balavoine, Chem. Commun. 1996, 527-528; b) G. Iftime, J.-C. Daran, E. Manoury, G. G. A. Balavoine, Organometallics 1996, 15, 4808-4815; c) M. Tsukazaki, M. Tinkl, A. Roglans, B. J. Chapell, N, J. Taylor, V. Snieckus, J. Am. Chem. Soc. 1996, 118, 685-686.
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    • note
    • Optimization of the geometry was performed with the semi-empirical PM3(tm) procedure, as implemented in the SPARTAN package of programs.
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    • Obtained as described in: a) M. Catasús, A. Bueno, A. Moyano, M. A. Maestro, J. Mahía, J. Organomet. Chem. 2002, 642, 212-226. (R)-1 is also obtained in high enantiomeric purity by the same method or by the alternative procedure of: b) A. Patti, M. Lotz, P. Knochel, Tetrahedron: Asymmetry 2001, 12, 3375-3380.
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    • Obtained as described in: a) M. Catasús, A. Bueno, A. Moyano, M. A. Maestro, J. Mahía, J. Organomet. Chem. 2002, 642, 212-226. (R)-1 is also obtained in high enantiomeric purity by the same method or by the alternative procedure of: b) A. Patti, M. Lotz, P. Knochel, Tetrahedron: Asymmetry 2001, 12, 3375-3380.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3375-3380
    • Patti, A.1    Lotz, M.2    Knochel, P.3
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    • note
    • -1 in all experiments.
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    • Prepared from (E)-cinnamyl alcohol in 84 % yield according to the literature procedure: L. Engman, J. Org. Chem. 1993, 58, 2394-2401.
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    • The asymmetric rearrangement of 8 to (-)-9 catalyzed by a dimeric (di-μ-trifluoroacetate)palladium complex derived from (R)-N,N-dimethyl-2(- ferrocenyl)ethylamine occurred in 47 % yield with 47% ee; see: T. K. Hollis, L. E. Overman, Tetrahedron Lett. 1997, 38, 8837-8840.
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