Convenient synthesis and efficient resolution of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol

Tetrahedron Asymmetry

Volumn 14, Issue 10, 2003, Pages 1393-1396

  Tsubaki, Kazunori ^a   Morikawa, Hiroshi ^a   Tanaka, Hiroyuki ^a   Fuji, Kaoru ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,3' BIS(BENZYLOXY) 1,1' BINAPHTHALENE 2,2' DIOL; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DIASTEREOISOMER; OPTICAL RESOLUTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0038448217     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00219-2     Document Type: Article

References (19)

1. Examples of oligo(2,3-dioxyfunctionalized)naphthalenes connected at their 1,4-positions. (a) Habaue, S.; Seko, T.; Okamoto, Y. Macromolecules 2002, 35, 2437-2439;
2. (b) Tsubaki, K.; Tanaka, H.; Furuta, T.; Tanaka, K.; Kinoshita, T.; Fuji, K. Tetrahedron 2002, 58, 5611-5617;
3. (c) Fuji, K.; Furuta, T.; Tanaka, K. Org. Lett. 2001, 3, 169-171;
4. (d) Fuji, K.; Furuta, T.; Otsubo, T.; Tanaka, K. Tetrahedron Lett. 1999, 40, 3001-3004.
5. Luo Z., Liu Q., Gong L., Cui X., Mi A., Jiang Y. Angew. Chem., Int. Ed. 41:2002;4532-4535.
6. Luo Z., Liu Q., Gong L., Cui X., Mi A., Jiang Y. Chem. Commun. 2002;914-915.
7. Barhate N.B., Chen C.-T. Org. Lett. 4:2002;2529-2532.
8. Chu C.-Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981.
9. Hon S.-W., Li C.-H., Kuo J.-H., Barhate N.B., Liu Y.-H., Wang Y., Chen C.-T. Org. Lett. 4:2001;869-872.
10. Li X., Yang J., Kozlowski M.C. Org. Lett. 3:2001;1137-1140.
11. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S., Noji M., Koga K. J. Org. Chem. 64:1999;2264-2271.
12. Irie R., Masutani K., Katsuki T. Synlett. 2000;1433-1436.
13. Tanaka K., Furuta T., Fuji K., Miwa Y., Taga T. Tetrahedron: Asymmetry. 7:1996;2199-2202.
14. Weber E., Köhler H.-J., Reuter H. Chem. Ber. 122:1989;959-967.
15. Review on related binaphthyl derivatives. (a) Putala, M. Enantiomer 1999, 4, 243-262;
16. (b) Brussee, J.; Groenendijk, J. L.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319.
17. Z-Pro-OH, Boc-Ala-OH, Boc-Val-OH, Boc-Ile-OH, Boc-Pro-OH, Boc-Tyr-OH, Boc-Asn-OH, Boc-His-OH, Boc-His(Boc)-OH, Boc-Met-OH, and Boc-Asp-OH were screened Recently, efficient chromatographic resolution of BINOLs using amino acid derivatives was reported. Panchal, B. M.; Einhorn, C.; Einhorn, J. Tetrahedron Lett. 2002, 43, 9245-9248.
18. Shan Z., Xiong Y., Zhao D. Tetrahedron. 55:1999;3893-3896.
19. Periasamy M., Venkatraman L., Sivakumar S., Sampathkumar N., Ramanathan C.R. J. Org. Chem. 64:1999;7643-7645.