Preparation of enantiopure biimidazoline ligands and their use in asymmetric catalysis

Organic and Biomolecular Chemistry

Volumn 2, Issue 14, 2004, Pages 1995-2002

  Boland, Nicola A ^a   Casey, Mike ^a   Hynes, Stephen J ^a   Matthews, Jonathan W ^a   Müller Bunz, Helge ^a   Wilkes, Philippa ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHROMATOGRAPHY; CRYSTAL STRUCTURE; DERIVATIVES; REACTION KINETICS; STEREOCHEMISTRY; X RAYS;

ASYMMETRIC CATALYSIS; CHIRAL LIGANDS; ENANTIOPURE BIIMIDAZOLINE LIGANDS; METAL-CATALYZED REACTIONS;

AROMATIC COMPOUNDS;

EID: 3843093821     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b407743c     Document Type: Article

References (72)

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53. The individual diastereomers could be obtained by using the individual enantiomers of the diamine, which are commercially available, but we prepared a mixture in order to carry out an initial evaluation of both diastereomeric ligands.
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58. Reaction of malonate with cyclohexenyl acetate using a selection of the ligands gave uniformly low (<20%) ee values.
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60. For examples of the use of diamine ligands, see: (a) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683; (b) H. Kubota, M. Nakajima and K. Koga, Tetrahedron Lett., 1993, 34, 8135; (c) J. Y. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; (d) P. G. Andersson, A. Harden, D. Tanner and P. O. Norrby, Chem. Eur. J., 1995, 1, 12; (e) P. Gamez, B. Dunjic, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109; (f) D. Tanner, F. Johansson, A. Harden and P. G. Andersson, Tetrahedron, 1998, 54, 15731.
61. For examples of the use of diamine ligands, see: (a) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683; (b) H. Kubota, M. Nakajima and K. Koga, Tetrahedron Lett., 1993, 34, 8135; (c) J. Y. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; (d) P. G. Andersson, A. Harden, D. Tanner and P. O. Norrby, Chem. Eur. J., 1995, 1, 12; (e) P. Gamez, B. Dunjic, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109; (f) D. Tanner, F. Johansson, A. Harden and P. G. Andersson, Tetrahedron, 1998, 54, 15731.
62. For examples of the use of diamine ligands, see: (a) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683; (b) H. Kubota, M. Nakajima and K. Koga, Tetrahedron Lett., 1993, 34, 8135; (c) J. Y. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; (d) P. G. Andersson, A. Harden, D. Tanner and P. O. Norrby, Chem. Eur. J., 1995, 1, 12; (e) P. Gamez, B. Dunjic, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109; (f) D. Tanner, F. Johansson, A. Harden and P. G. Andersson, Tetrahedron, 1998, 54, 15731.
63. For examples of the use of diamine ligands, see: (a) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683; (b) H. Kubota, M. Nakajima and K. Koga, Tetrahedron Lett., 1993, 34, 8135; (c) J. Y. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; (d) P. G. Andersson, A. Harden, D. Tanner and P. O. Norrby, Chem. Eur. J., 1995, 1, 12; (e) P. Gamez, B. Dunjic, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109; (f) D. Tanner, F. Johansson, A. Harden and P. G. Andersson, Tetrahedron, 1998, 54, 15731.
64. For examples of the use of diamine ligands, see: (a) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683; (b) H. Kubota, M. Nakajima and K. Koga, Tetrahedron Lett., 1993, 34, 8135; (c) J. Y. Kang, W. O. Cho and H. G. Cho, Tetrahedron: Asymmetry, 1994, 5, 1347; (d) P. G. Andersson, A. Harden, D. Tanner and P. O. Norrby, Chem. Eur. J., 1995, 1, 12; (e) P. Gamez, B. Dunjic, F. Fache and M. Lemaire, Tetrahedron: Asymmetry, 1995, 6, 1109; (f) D. Tanner, F. Johansson, A. Harden and P. G. Andersson, Tetrahedron, 1998, 54, 15731.
65. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
66. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
67. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
68. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
69. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
70. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
71. For recent examples of the use of other NN ligands, see: (a) R. Stranne and C. Moberg, Eur. J. Org. Chem., 2001, 2191; (b) C. Bolm, O. Simic and M. Martin, Synlett, 2001, 1878; (c) I. Abrunhosa, M. Gulea, J. Levillain and S. Masson, Tetrahedron: Asymmetry, 2001, 12, 2851; (d) A. V. Malkov, I. R. Baxendale, M. Bella, V. Langer, J. Fawcett, D. R. Russell, D. J. Mansfield, M. Valko and P. Kocovsky, Organometallics, 2001, 20, 673; (e) M. A. Pericas, C. Puigjaner, A. Riera, A. Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller and M. Rocamora, Chem. Eur. J., 2002, 8, 4164; (f) D. Sepac, M. Roje, Z. Hamersak and V. Sunjic, Croat. Chem. Acta, 2003, 76, 235; (g) J. Bayardon and D. Sinou, Tetrahedron Lett., 2003, 44, 1449.
72. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed., 1993, 32, 566.