Convenient and highly efficient chromatographic resolution of BINOL and of 6,6′-dibromo-BINOL via N(α)-Boc-tryptophan esters

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9245-9248

  Panchal, Bhavesh M ^a   Einhorn, Cathy ^a   Einhorn, Jacques ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Amino acids and derivatives; Biaryls; Column chromatography; Resolution

Indexed keywords

6,6' DIBROMO[1,1']BINAPHTHALENYL 2,2' DIOL; ALCOHOL DERIVATIVE; AMINO ACID; ESTER DERIVATIVE; N BUTYLOXYCARBONYLTRYPTOPHAN; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RACEMIC MIXTURE; THIN LAYER CHROMATOGRAPHY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037049198     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02268-2     Document Type: Article

References (30)

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19. Various direct chromatographic resolutions of BINOL and of other axially chiral biphenols have also been described via chiral HPLC, some of them with very large enantioseparations, see for example: (a) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036-4048. Some of these separations have been performed on stationary phases amenable to large-scale simulated moving bed (SMB) technology. See: (b) Negawa, M.; Shoji, F. J. Chromatogr. 1992, 590, 113-117; (c) Ogawa, T.; Ohtsu, Y. Nippon Kagaku Kaishi 1997, 3, 201-206; (d) Kasuya, N.; Nakashima, J.; Kubo, T.; Sawatari, A.; Habu, N. Chirality 2000, 12, 670-674. For miscellaneous other resolutions of 1, see: (e) Du, H.; Ji, B.; Wang, Y.; Sun, J.; Meng, J.; Ding, K. Tetrahedron Lett. 2002, 43, 5273-5276, and references cited therein.
20. Various direct chromatographic resolutions of BINOL and of other axially chiral biphenols have also been described via chiral HPLC, some of them with very large enantioseparations, see for example: (a) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036-4048. Some of these separations have been performed on stationary phases amenable to large-scale simulated moving bed (SMB) technology. See: (b) Negawa, M.; Shoji, F. J. Chromatogr. 1992, 590, 113-117; (c) Ogawa, T.; Ohtsu, Y. Nippon Kagaku Kaishi 1997, 3, 201-206; (d) Kasuya, N.; Nakashima, J.; Kubo, T.; Sawatari, A.; Habu, N. Chirality 2000, 12, 670-674. For miscellaneous other resolutions of 1, see: (e) Du, H.; Ji, B.; Wang, Y.; Sun, J.; Meng, J.; Ding, K. Tetrahedron Lett. 2002, 43, 5273-5276, and references cited therein.
21. Various direct chromatographic resolutions of BINOL and of other axially chiral biphenols have also been described via chiral HPLC, some of them with very large enantioseparations, see for example: (a) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036-4048. Some of these separations have been performed on stationary phases amenable to large-scale simulated moving bed (SMB) technology. See: (b) Negawa, M.; Shoji, F. J. Chromatogr. 1992, 590, 113-117; (c) Ogawa, T.; Ohtsu, Y. Nippon Kagaku Kaishi 1997, 3, 201-206; (d) Kasuya, N.; Nakashima, J.; Kubo, T.; Sawatari, A.; Habu, N. Chirality 2000, 12, 670-674. For miscellaneous other resolutions of 1, see: (e) Du, H.; Ji, B.; Wang, Y.; Sun, J.; Meng, J.; Ding, K. Tetrahedron Lett. 2002, 43, 5273-5276, and references cited therein.
22. Various direct chromatographic resolutions of BINOL and of other axially chiral biphenols have also been described via chiral HPLC, some of them with very large enantioseparations, see for example: (a) Yashima, E.; Yamamoto, C.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 4036-4048. Some of these separations have been performed on stationary phases amenable to large-scale simulated moving bed (SMB) technology. See: (b) Negawa, M.; Shoji, F. J. Chromatogr. 1992, 590, 113-117; (c) Ogawa, T.; Ohtsu, Y. Nippon Kagaku Kaishi 1997, 3, 201-206; (d) Kasuya, N.; Nakashima, J.; Kubo, T.; Sawatari, A.; Habu, N. Chirality 2000, 12, 670-674. For miscellaneous other resolutions of 1, see: (e) Du, H.; Ji, B.; Wang, Y.; Sun, J.; Meng, J.; Ding, K. Tetrahedron Lett. 2002, 43, 5273-5276, and references cited therein.
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25. 1H NMR spectroscopy. See Ref. 7 for similar observations.
26. -1.
27. -1. Furthermore, as variation of the enantiomeric purity of the amino acid derivatives depending on the supplier have been reported, we have also checked starting 3a, after its preliminary derivatisation into 3b with diazomethane.
28. 11 Further elution of the column gave 3b (1.049 g, 3.293 mmol, 83% yield) identical to the sample obtained from 5a.
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