Chiral 8-amino substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethylmethanoquinolines as chiral ligands for enantioselective catalysis: Palladium catalysed allylic substitution and addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2571-2578

  Chelucci, Giorgio ^a   Pinna, Gerard A ^a   Saba, Antonio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; LIGAND; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030847032     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00275-9     Document Type: Article

References (45)

1. Collomb, P.; von Zelewsky, A. Tetrahedron: Asymmetry, 1995, 6, 2903.
2. Chelucci, G.; Cabras, M.A. Tetrahedron: Asymmetry, 1996, 7, 965.
3. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. Chelucci, G.; Marchetti, M. Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M.A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Basoli, C.; Botteghi, C.; Cabras, M.A.; Chelucci, G.; Marchetti, M. J. Organomet. Chem., 1995, 488, C20-C22. Chelucci, G.; Cabras, M.A.; Saba, A. J. Mol. Catal., 1995, 95, L7-L10.
4. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. Chelucci, G.; Marchetti, M. Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M.A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Basoli, C.; Botteghi, C.; Cabras, M.A.; Chelucci, G.; Marchetti, M. J. Organomet. Chem., 1995, 488, C20-C22. Chelucci, G.; Cabras, M.A.; Saba, A. J. Mol. Catal., 1995, 95, L7-L10.
5. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. Chelucci, G.; Marchetti, M. Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M.A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Basoli, C.; Botteghi, C.; Cabras, M.A.; Chelucci, G.; Marchetti, M. J. Organomet. Chem., 1995, 488, C20-C22. Chelucci, G.; Cabras, M.A.; Saba, A. J. Mol. Catal., 1995, 95, L7-L10.
6. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. Chelucci, G.; Marchetti, M. Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M.A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Basoli, C.; Botteghi, C.; Cabras, M.A.; Chelucci, G.; Marchetti, M. J. Organomet. Chem., 1995, 488, C20-C22. Chelucci, G.; Cabras, M.A.; Saba, A. J. Mol. Catal., 1995, 95, L7-L10.
7. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. Chelucci, G.; Marchetti, M. Sechi, B. J. Organomet. Chem., 1997, in press. Chelucci, G.; Cabras, M.A.; Botteghi, C.; Basoli, C.; Marchetti, M. Tetrahedron: Asymmetry, 1996, 7, 885. Basoli, C.; Botteghi, C.; Cabras, M.A.; Chelucci, G.; Marchetti, M. J. Organomet. Chem., 1995, 488, C20-C22. Chelucci, G.; Cabras, M.A.; Saba, A. J. Mol. Catal., 1995, 95, L7-L10.
8. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
9. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
10. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
11. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
12. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
13. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
14. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
15. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
16. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
17. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
18. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
19. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
20. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
21. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
22. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
23. For a review on the application of pyridine ligands in asymmetric catalysis, see: Chelucci, G. Gazz. Chim. Ital, 1992, 122, 89. For more recent applications, see: Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry, 1996, 7, 653. Ito, K.; Yoshitake, M. Heterocycles, 1996, 42, 305. Ito, K.; Yoshitake, M., Katsuki, T. Tetrahedron, 1996, 52, 3905. Zhao, S.H.; Ortiz, P.R.; Keyss, B.A.; Davenport, K.G. Tetrahedron Lett., 1996, 37, 2725. Dattagupta, A.; Singh, V.K. Tetrahedron Lett., 1996, 37, 2633. Evans, D.A.; Murry, J.A.; Cozlosowski, M.C. J. Am. Chem. Soc., 1996, 118, 5814. Sablong, R.; Osborn, A. Tetrahedron Lett., 1996, 37, 4937. Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett., 1996, 37, 4475. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett., 1996, 37, 79. Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry, 1995, 6, 2487. Fung, W.-H.; Cheng, W.-C; Yu, W.-Y.; Che, C.-M.; Mark, T. C. W. J. Chem. Soc., Chem. Comm. 1995, 2007. Christenson, D. L.; Tokar, C. J.; Tolman., W. B. Organometallics, 1995, 14, 2148. Brunner, H.; Hernichs, C. Tetrahedron: Asymmetry, 1995, 6, 653. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem., 1995, 60, 3585. Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl., 1991, 30, 49.
24. Gamez, P.; Dunjic, B.; Fache, F.; Lamaire, M. J. Chem. Soc., Chem. Comm., 1994, 1417.
25. Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165.
26. Reimann, E.: Reitz, R. Liebigs Ann. Chem., 1975, 1881. Bertucci, C.; Uccello-Barretta, G.; Chelucci, G.; Botteghi, C. Gazz. Chim. It., 1990, 120, 263.
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28. A similar result has been recently observed: Rae, D.R.; Strachan, J. J. Chem. Research (S), 1996, 14.
29. N2 displacement reactions on related compounds has been observed: Fohlisch, B.; Schwaiger, G. Annalen, 1975, 1.
30. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
31. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
32. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
33. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
34. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
35. Trost, M.B.; Van Vranken, D.L. Chem. Rev., 1996, 96, 395. Reiser, O. Angew. Chem., 1993, 105, 576; Angew. Chem. Int. Ed. Engl., 1993, 32, 547. Hayashi, T., in Catalytic Asymmetric Synthesis, Ed. Ojima, VCH, Weinheim, 1993. Frost, C.G.; Howarth, J.; Williams, J.M.J. Tetrahedron: Asymmetry, 1992, 3, 1089. Dawson, G.J.; Williams, J.M.J.; Coote, S.J. Tetrahedron: Asymmetry, 1995, 6, 2535, and references therein.
36. Togni, A.; Venanzi, L.M. Angew. Chem. Int. Ed. Engl., 1994, 33, 497.
37. Frost, C.G.; Williams, J.M.J. Tetrahedron Lett., 1993, 34, 2015. Allen, J.V.; Coote, S.J.; Dawson, G.J.; Frost, C.G.; Martin, C.J.; Williams, J.M.J. J. Chem. Soc., Perkin Trans. 1, 1994, 15, 2065.
38. Frost, C.G.; Williams, J.M.J. Tetrahedron Lett., 1993, 34, 2015. Allen, J.V.; Coote, S.J.; Dawson, G.J.; Frost, C.G.; Martin, C.J.; Williams, J.M.J. J. Chem. Soc., Perkin Trans. 1, 1994, 15, 2065.
39. During the drafting of this paper the synthesis of new amino-pyridines prepared for enantioselective palladium catalysed allylic substitutions was described. However, no data on the enantioselective ability of these ligands was reported: Sweet, J.A.; Cavallari, J.M.; Price, W.A.; Ziller, J.W.; McGrath, D.V. Tetrahedron: Asymmetry, 1997, 8, 207. Moreover, it has been very recently reported that N-(2-pyridylmethyl)sulfoximines were able to control enantioselective Pd-catalysed allylic substitutions, enantioselectivities up to 73% were obtained: Bolm, C.; Kaufmann, D.; Zehnder, M.; Neuburger, M. Tetrahedron Letters, 1996, 37, 3985.
40. During the drafting of this paper the synthesis of new amino-pyridines prepared for enantioselective palladium catalysed allylic substitutions was described. However, no data on the enantioselective ability of these ligands was reported: Sweet, J.A.; Cavallari, J.M.; Price, W.A.; Ziller, J.W.; McGrath, D.V. Tetrahedron: Asymmetry, 1997, 8, 207. Moreover, it has been very recently reported that N-(2-pyridylmethyl)sulfoximines were able to control enantioselective Pd-catalysed allylic substitutions, enantioselectivities up to 73% were obtained: Bolm, C.; Kaufmann, D.; Zehnder, M.; Neuburger, M. Tetrahedron Letters, 1996, 37, 3985.
41. Trost, B.M.; Murphy, D.J. Organometallics, 1985, 4, 1143.
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43. Ishizaki, M.; Hoshino, O. Tetrahedron: Asymmetry, 1994, 5, 1901; Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry, 1994, 5, 441.
44. Brunner, H.; Reiter, B.; Rielp, G. Chem. Ber., 1984, 117, 1330.
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