Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 648-657

  Anderson, Carolyn E ^a   Donde, Yariv ^a   Douglas, Christopher J ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; DIMERS; PALLADIUM; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL);

CHIRAL ALLYLIC AMINES; FERROCENYLOXAZOLINE PALLADACYCLIC (FOP); PRECATALYSTS; SILVER TRIFLUOROACETATE;

AMINES;

BENZENE DERIVATIVE; FERROCENYLOXAZOLINE PALLADACYCLE; N (4 METHOXYPHENYL)BENZAMIDE; N (4 METHOXYPHENYL)BENZIMIDATE; N ARYLTRIFLUOROACETIMIDATE; PALLADIUM COMPLEX; SILVER DERIVATIVE; SILVER TRIFLUOROACETATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PROTEIN MOTIF; ROOM TEMPERATURE;

ALLYLAMINE; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; FERROUS COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 12344337113     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048490r     Document Type: Article

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33. The authors have deposited coordinates for these compounds with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
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35. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
36. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
37. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
38. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
39. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
40. For X-ray crystallography of chloride-bridged ferrocenyl palladacycles, see: (a) Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y., K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984. (b) Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636. (c) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557-1561. (d) Wu, Y. J.; Cui, X. L.; Du, C. X.; Wang, W. L.; Guo, R. Y.; Chen, R. F. J. Chem. Soc., Dalton Trans. 1998, 3727-3730. (e) Zhao, G.; Wang, Q. G-.; Mak, T. C. W. Polyhedron 1998, 18, 577-584. (f) López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530. (g) Reference 3d.
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58. This activation likely involves both salt metathesis, exchanging the iodide of the palladacycle for trifluoroacetate, in addition to oxidation of the ferrocene to a ferrocenium ion by the Ag(I). For studies with precatalyst 9a, see ref 6.
59. 29
60. Anderson, C. E. Ph.D. Dissertation, University of California, Irvine, 2003.