Practical preparation and resolution of 1-(2′-diphenylphosphino-1′-naphthyl)isoquinoline: A useful ligand for catalytic asymmetric synthesis

Organic Process Research and Development

Volumn 7, Issue 3, 2003, Pages 379-384

  Lim, Chung Woo ^a   Tissot, Olivier ^a   Mattison, Andrew ^a   Hooper, Mark W ^a   Brown, John M ^a   Cowley, Andrew R ^a   Hulmes, David I ^a,b   Blacker, A John ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Avecia Biologics Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2' DIPHENYLPHOSPHINO 1' NAPHTHYL)ISOQUINOLINE; ISOQUINOLINE DERIVATIVE; LIGAND; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENANTIOMER; X RAY ANALYSIS;

EID: 0038384666     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034007n     Document Type: Article

References (45)

1. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743.
2. Brown, J. M.; Hulmes, D. I.; Layzell, T. P. Chem. Commun. 1993, 1673; Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem. Eur. J. 1999, 5, 1320. Brown, J. M. (Isis Innovation Ltd., UK). PCT Int. Appl. Wo 9513284, 1995.
3. Brown, J. M.; Hulmes, D. I.; Layzell, T. P. Chem. Commun. 1993, 1673; Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem. Eur. J. 1999, 5, 1320. Brown, J. M. (Isis Innovation Ltd., UK). PCT Int. Appl. Wo 9513284, 1995.
4. Brown, J. M.; Hulmes, D. I.; Layzell, T. P. Chem. Commun. 1993, 1673; Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem. Eur. J. 1999, 5, 1320. Brown, J. M. (Isis Innovation Ltd., UK). PCT Int. Appl. Wo 9513284, 1995.
5. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
6. Rautenstrauch, V.; Challand, R.; Churlaud, R.; Morris, R. H.; Abdur-Rashid, K.; Brazi, E.; Mimoun, H. (Firmenich S. A., Switz.). PCT Int. Appl. Wo 0222526, 2002.
7. Consiglio, G.; Gsponer, A. Polym. Mater. Sci. Eng. 2002, 87, 78.
8. Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
9. Faller, J. W.; Grimmond, B. J. Organometallics 2001, 20, 2454.
10. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
11. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
12. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
13. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
14. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
15. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
16. Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157; Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043; Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539; Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 804; Rabeyrin, C.; Nguefack, C.; Sinou, D. Tetrahedron Lett. 2000, 41, 7461; Tillack, A.; Koy, C.; Michalik, D.; Fischer, C. J. Organomet. Chem. 2000, 603, 116; Yamashita, M.; Nagata, T. (Takeda Chemical Industries, Ltd., Japan). PCT Int. Appl. Wo 0119777, 2001.
17. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
18. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
19. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
20. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
21. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
22. For recent examples, see: Kwong, F. Y.; Yang, Q. C.; Mak, T. C. W.; Chan, A. S. C.; Chan, K. S. J. Org. Chem. 2002, 67, 2769; Demay, S.; Volant, F.; Knochel, P. Angew. Chem., Int. Ed. 2001, 40, 1235; Ruiz, J. L.; Flor, T.; Bayon, J. C. Inorg. Chem. Commun. 1999, 2, 484; Kang, J. Y.; Lee, J. H.; Kim, J. B.; Kim, G. J. Chirality 2000, 12, 378. The quinazoline ligands related to QUINAP prepared by Guiry and co-workers are comparably effective for the asymmetric hydroboration of disubstituted arylalkenes: Lacey, P. M.; McDonnell, C. M.; Guiry, P. J. Tetrahedron Lett. 2000, 41, 2475; McCarthy, M.; Hooper, M. W.; Guiry, P. J. Chem. Commun. 2000, 1333.
23. For C-C bond-forming procedures directly from the boronate ester, see: Chen, A. C.; Ren, L.; Crudden, C. M. Chem. Commun. 1999, 611; Chen, A.; Ren, L.; Crudden, C. M. J. Org. Chem. 1999, 64, 9704.
24. For C-C bond-forming procedures directly from the boronate ester, see: Chen, A. C.; Ren, L.; Crudden, C. M. Chem. Commun. 1999, 611; Chen, A.; Ren, L.; Crudden, C. M. J. Org. Chem. 1999, 64, 9704.
25. Fernandez, E.; Hooper, M. W.; Knight, F. I.; Brown, J. M. Chem. Commun. 1997, 173; Fernandez, E.; Maeda, K.; Hooper, M. W.; Brown, J. M. Chem. Eur. J. 2000, 6, 1840.
26. Fernandez, E.; Hooper, M. W.; Knight, F. I.; Brown, J. M. Chem. Commun. 1997, 173; Fernandez, E.; Maeda, K.; Hooper, M. W.; Brown, J. M. Chem. Eur. J. 2000, 6, 1840.
27. Maeda, K.; Brown, J. M. Chem. Commun. 2002, 310.
28. Segarra, A. M.; Guerrero, R.; Claver, C.; Fernandez, E. Chem. Commun. 2001, 1808. Segara, A. M.; Guerro, R.; Claver, C.; Fernandez, E. Chem. - Eur. J. 2003, 9, 191.
29. Segarra, A. M.; Guerrero, R.; Claver, C.; Fernandez, E. Chem. Commun. 2001, 1808. Segara, A. M.; Guerro, R.; Claver, C.; Fernandez, E. Chem. - Eur. J. 2003, 9, 191.
30. Both enantiomers of QUINAP are commercially available via Strem.
31. Cai, D. W.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
32. Kwong, F. Y.; Chan, A. S. C.; Chan, K. S. Tetrahedron 2000, 56, 8893.
33. Flack H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143.
34. Aplin, R. T.; Doucet, H.; Hooper, M. W.; Brown, J. M. Chem. Commun. 1997, 2097.
35. Alcock, N. W.; Hulmes, D. I.; Brown, J. M. Chem. Commun. 1995, 395.
36. 3) has been checked to consistency and accords with values obtained from the equipment at the National Chiroptical Centre, KCL. It therefore replaces the value of ± 153 quoted in the original paper (ref 1).
37. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; John Wiley and Sons: New York, 1981; pp 307 ff; Eliel, E. L.; Wilen S. H.; Mander L. N. Stereochemistry of Carbon Compounds; John Wiley and Sons: New York, 1994; Chapter 7.3, p 350.
38. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; John Wiley and Sons: New York, 1981; pp 307 ff; Eliel, E. L.; Wilen S. H.; Mander L. N. Stereochemistry of Carbon Compounds; John Wiley and Sons: New York, 1994; Chapter 7.3, p 350.
39. Ikehara, M. Chem. Pharm. Bull., 1954, 2, 111.
40. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
41. Allen, D. G.; McLaughlin, G. M.; Robertson, G. B.; Steffen, W. L.; Salem, G.; Wild, S. B. Inorg. Chem. 1982, 21, 1007.
42. Baker, K. V.; Brown J. M.; Hughes, N.; Skarnulis A. J.; Sexton A. J. Org. Chem, 1991, 56, 698.
43. Otwinowski, Z. Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276.
44. Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A.; Burla, M. C.; Polidori G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
45. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I. CRYSTALS; Chemical Crystallography Laboratory: Oxford, UK, 2001; issue 11.