Evidence for the structure of the enantioactive ligand in the phosphine-copper-catalyzed addition of diorganozinc reagents to imines

Angewandte Chemie - International Edition

Volumn 43, Issue 47, 2004, Pages 6525-6528

  Côté, Alexandre ^a   Boezio, Alessandro A ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Copper; Imino compounds; Nucleophilic addition; Oxidation; Phosphine ligands

Indexed keywords

COPPER COMPOUNDS; OXIDATION; PHOSPHATES;

DIORGANOZINE REAGENTS; MONOPHOSPHINE OXIDE 2; N-DIPHENYLPHOSPHINOYLIMINES;

CATALYSIS;

COPPER DERIVATIVE; IMINE; PHOSPHINE DERIVATIVE; REAGENT;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; LIGAND BINDING; OXIDATION;

EID: 11144271344     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461920     Document Type: Article

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40. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].
41. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].
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44. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].
45. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].
46. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].
47. For some examples of monophosphane ligands bearing an additional coordinating heteroatom used in asymmetric catalysis: a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615; Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568; b) J. M. Brown, D. I. Hulmes, P. I. Guiry, Tetrahedron 1994, 50, 4493-5006; c) H. Kodama, T. Taiji, T. Ohta, I. Furukawa, Tetrahedron: Asymmetry 2000, 11, 4009-4015; d) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888; e) S. Vyskocil, M. Smrcina, V. Hanus, M. Polasek, P. Kocovsky, J. Org. Chem. 1998, 63, 7738-7748; f) T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261-1268; g) T. Hayashi, H. Iwamura, M. Naito, Y. Matsumoto, Y. Uozumi, J. Am. Chem. Soc. 1994, 116, 775-776; h) A. Chieffi, K. Kamikawa, J. Åhman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1903; i) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769-1772; Ref. [6], [7 b,c].