Efficient synthesis of chiral 1,1′-binaphthalenes by the asymmetric suzuki-miyaura reaction: Dramatic synthetic improvement by simple purification of naphthylboronic acids

Chemistry - A European Journal

Volumn 12, Issue 36, 2006, Pages 9346-9352

  Genov, Miroslav ^a   Almorín, Antonio ^a   Espinet, Pablo ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Asymmetric synthesis; Binaphthyls; Boronic acids; Enantioselectivity; Suzuki miyaura reaction

Indexed keywords

BROMINE COMPOUNDS; DERIVATIVES; ORGANIC ACIDS; PHOSPHORUS COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; BINAPHTHYLS; BORONIC ACIDS; ENANTIOSELECTIVITY; SUZUKI-MIYAURA REACTION;

NAPHTHALENE;

BORONIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

BORONIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 33845745460     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600616     Document Type: Article

References (30)

1. a) L. Pu, Chem. Rev. 1998, 98, 2405-2494;
2. b) M. Putala, Enantiomer 1999, 4, 243-262.
3. G. Bringman, M. Breuning, Synthesis 1999, 525-558.
4. D. M. Hall, E. E. Terner, J. Chem. Soc. 1955, 1242.
5. N. Maigrot, J. P. Mazaleyrat, Synthesis 1985, 317-319.
6. E. P. Kyba, G. W. Gokel, F. de Jong, K. Koga, L. R. Sousa, M. G. Siegel, L. Kaplan, G. D. Y. Sogah, D. J. Cram, J. Org. Chem. 1977, 42, 4173-4184.
7. K. J. Brown, M. S. Berry, J. R. Murdoch, J. Org. Chem. 1985, 50, 4345-4349.
8. T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8156.
9. H. Iia, O. Baron, A. J. Wanger, P. Knochel, Chem. Commun. 2006, 583-593.
10. O. Baidoin, Eur. J. Org. Chem. 2005, 4223-4229, and references herein.
11. A. N. Cammidge, K. V. L. Crépy, Chem. Commun. 2000, 1723-1724.
12. A. N. Cammidge, K. V. L. Crépy. Tetrahedron 2004, 60, 4377-4386.
13. J. F. Jennsen, M. Johannsen, Org. Lett. 2003, 5, 3025-3028.
14. J. Yin, L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051-12052.
15. A.-S. Castanet, F. Colobert, P.-E. Broutin, M. Obringer, Tetrahedron: Asymmetry 2002, 13, 659-665.
16. K. Mikami, T. Miyamoto, M. Hatano, Chem. Commun. 2004, 2082-2083.
17. For examples in which this problem seems to have been a factor see experimental details in rufs. [11,][17,][18], as well as: a) A. C. Spivey, Z. Fujiang, M. B. Mitchell, S. G Davey, R. L. Jarvcst, J. Org. Chem. 2003, 68, 7379-7385;
18. b) G. Bringmann, A. Hamm, M. Schraut, Org. Lett. 2003, 5, 2805-2808:
19. G. Bringmann, A. Hamm, M. Schraut. Org. Lett. 2003, 5, 2805-2808.
20. A. C. Spivey, T. Fekner, S. E. Spey, H. Adams, J. Org. Chem. 1999, 64, 9430-9443.
21. J. Clews, A. D. M. Curtis, H. Malkin, Tetrahedron 2000, 56, 8735-8746.
22. N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566.
23. W. R. Cullen, F. W. B. Einstein, C.-H. Huang, A. C. Willis, E.-S. Yeh, J. Am. Chem. Soc. 1980, 102, 988-993.
24. A. N. Cammidge, K. V. L. Crépy, J. Org. Chem. 2003, 68, 6832-6835.
25. J. C. Anderson, S. P. Maddaford, B. A. Keay, J. Org. Chem. 1996, 61, 9556-9599.
26. a) E. M. Suh, Y. Kishi, J. Am. Chem. Soc. 1994, 116, 11205-11206;
27. b) K. C. Nicolaou, S. Natarajan, H. Li, N. F. Jain, R. Hughes, M. E. Solomon, J. M. Ramajulu, C. N. C. Boddy, M. Takayanagi, Angew. Chem. 1998, 110, 2872-2878;
28. D. L. Boder, S. Miyazaki, S. H. Kim, J. W. Hu, O. Loiseleur, S. L. Castle, J. Am. Chem. Soc. 1999, 121, 3226-3227.
29. H. W. I. Peerlings, E. W. Meijer, Eur. J. Org. Chem. 1998, 573-577.
30. J. J. G. S. van Es, H. A. M. Biemans, E. W. Meijer, Tetrahedron: Asymmetry 1997, 8, 1825-1831.