Synthesis, resolution and crystallographic characterization of a new C2-symmetric planar-chiral bipyridine ligand: Application to the catalytic enantioselective cyclopropanation of olefins

Chemical Communications

Volumn , Issue 5, 2000, Pages 377-378

  Rios, Ramon ^a   Liang, Jack ^a   Lo, Michael M C ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LIGAND; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLOGRAPHY; ENANTIOMER; SYNTHESIS;

EID: 0034615645     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909457a     Document Type: Article

References (38)

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6. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
7. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
8. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
9. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
10. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
11. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
12. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
13. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
14. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
15. 2 addition to benzaldehyde: C. Bolm, M. Zehnder and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205; P. Collomb and A. von Zelewsky, Tetrahedron: Asymmetry, 1998, 9, 3911; nickel-catalyzed conjugate addition to enones: C. Bolm and M. Ewald, Tetrahedron Lett., 1990, 31, 5011; rhodium-catalyzed transfer hydrogenation of ketones: S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron: Asymmetry, 1990, 1, 635; copper-catalyzed ring expansion of oxetanes to tetrahydrofurans: K. Ito and T. Katsuki, Chem. Lett., 1994, 1857; palladium-catalyzed allylic alkylation: E. Pena-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Akermark and P. Helquist, J. Am. Chem. Soc., 1996, 118, 4299; G. Chelucci, G. A. Pinna and A. Saba, Tetrahedron: Asymmetry, 1998, 9, 531; zinc-catalyzed allylation of aldehydes: H.-L. Kwong, K.-M. Lau, W.-S. Lee and W.-T. Wong, New J. Chem., 1999, 23, 629.
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