Selective preparation of optically pure (R,R)-1,1':5',1''- ternaphthalene-2,2',6',2''-tetraol: A new higher homolog of BINOL

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6487-6490

  Sugimura, Takashi ^a   Inoue, Shintaro ^a   Tai, Akira ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1':5',1'' TERNAPHTHALENE 2,2',6',2'' TETRAOL; NAPHTHOL DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032171317     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01381-1     Document Type: Article

References (19)

1. 1. R. Noyori Chem. Soc. Rev. 1989;18:187-208. J. K. Whitesell Chem. Rev. 1989;89:1581-1590. C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori Synthesis 1992:503-517.
2. 1. R. Noyori Chem. Soc. Rev. 1989;18:187-208. J. K. Whitesell Chem. Rev. 1989;89:1581-1590. C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori Synthesis 1992:503-517.
3. 1. R. Noyori Chem. Soc. Rev. 1989;18:187-208. J. K. Whitesell Chem. Rev. 1989;89:1581-1590. C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori Synthesis 1992:503-517.
4. 2. M. Belohradsky, M. Budesinsky, J. Gunterova, J. Hodacova, P. Holy, J. Zavada, I. Cisarova, J. Podlaha Tetrahedron 1996;52:11013-11024.
5. 3. T. Sugimura, H. Yamada, S. Inoue, A. Tai Tetrahedron: Asymmetry 1997;8:649-655.
6. 4. The Mitsunobu reaction was carried out with tributylphosphine (1.2 equivalents) and diethyl azodicarboxylate (1.2 eq.) in THF at room temperature.
7. 3-THF), and de-acetylation (NaOH in methanol, 97% for two steps).
8. 3) δ 152.7, 151.3, 133.0, 129.8, 129.1, 128.8, 127.7, 127.5, 127.0, 126.1, 124.3, 118.0, 116.8, 110.6, 77.3, 74.1, 73.8, 45.3, 21.2, 20.9.
9. 3) δ 154.9, 153.4, 133.7, 130.4, 130.3, 129.4, 128.0, 127.8, 126.6, 126.2, 124.1, 123.8, 123.3, 119.2, 75.4, 74.7, 42.2, 29.9, 22.7, 22.6.
10. 3) δ 152.7, 151.4, 151.3, 133.4, 131.6, 129.5, 128.5, 127.6, 124.3, 124.2, 124.2, 119.1, 119.1, 117.8, 110.9.
11. 9. Chiralpak AD (Daicel Chemical Industry, Ltd.) eluted with hexane/ethanol/trifluoroacetic acid (85/15/0.5, flow rate 0.5 ml/min). An authentic sample of racemic 1 was prepared by copper catalyzed air oxidation (see ref. 12) of a mixture of 2-naphthol and 2,6-naphthodiol followed by silica gel chromatography. Retention time for (R,R)-1, 54 min; for (S,S)-1, 76 min.
12. 10. T. Sugimura J. Synth. Org. Chem. Jpn. 1997;55:517-523.
13. 11. H. F. Chow, M. K. Ng Tetrahedron: Asymmetry 1996;7:2251-2262. K. Tanaka, T. Furuta, K. Fuji, Y. Miwa, T. Taga Tetrahedron: Asymmetry 1996;7:2199-2202. C. J. Li, D. Wang, W. T. Slaven IV Tetrahedron Lett. 1996;37:4459-4462. W. S. Huang, Q. S. Hu, X. F. Zheng, J. Anderson, L. Pu J. Am. Chem. Soc. 1997;119:4313-4314. Q. S. Hu, W. S. Huang, D. Vitharana, X. F. Zheng, L. Pu J. Am. Chem. Soc. 1997;119:12454-12464.
14. 11. H. F. Chow, M. K. Ng Tetrahedron: Asymmetry 1996;7:2251-2262. K. Tanaka, T. Furuta, K. Fuji, Y. Miwa, T. Taga Tetrahedron: Asymmetry 1996;7:2199-2202. C. J. Li, D. Wang, W. T. Slaven IV Tetrahedron Lett. 1996;37:4459-4462. W. S. Huang, Q. S. Hu, X. F. Zheng, J. Anderson, L. Pu J. Am. Chem. Soc. 1997;119:4313-4314. Q. S. Hu, W. S. Huang, D. Vitharana, X. F. Zheng, L. Pu J. Am. Chem. Soc. 1997;119:12454-12464.
15. 11. H. F. Chow, M. K. Ng Tetrahedron: Asymmetry 1996;7:2251-2262. K. Tanaka, T. Furuta, K. Fuji, Y. Miwa, T. Taga Tetrahedron: Asymmetry 1996;7:2199-2202. C. J. Li, D. Wang, W. T. Slaven IV Tetrahedron Lett. 1996;37:4459-4462. W. S. Huang, Q. S. Hu, X. F. Zheng, J. Anderson, L. Pu J. Am. Chem. Soc. 1997;119:4313-4314. Q. S. Hu, W. S. Huang, D. Vitharana, X. F. Zheng, L. Pu J. Am. Chem. Soc. 1997;119:12454-12464.
16. 11. H. F. Chow, M. K. Ng Tetrahedron: Asymmetry 1996;7:2251-2262. K. Tanaka, T. Furuta, K. Fuji, Y. Miwa, T. Taga Tetrahedron: Asymmetry 1996;7:2199-2202. C. J. Li, D. Wang, W. T. Slaven IV Tetrahedron Lett. 1996;37:4459-4462. W. S. Huang, Q. S. Hu, X. F. Zheng, J. Anderson, L. Pu J. Am. Chem. Soc. 1997;119:4313-4314. Q. S. Hu, W. S. Huang, D. Vitharana, X. F. Zheng, L. Pu J. Am. Chem. Soc. 1997;119:12454-12464.
17. 11. H. F. Chow, M. K. Ng Tetrahedron: Asymmetry 1996;7:2251-2262. K. Tanaka, T. Furuta, K. Fuji, Y. Miwa, T. Taga Tetrahedron: Asymmetry 1996;7:2199-2202. C. J. Li, D. Wang, W. T. Slaven IV Tetrahedron Lett. 1996;37:4459-4462. W. S. Huang, Q. S. Hu, X. F. Zheng, J. Anderson, L. Pu J. Am. Chem. Soc. 1997;119:4313-4314. Q. S. Hu, W. S. Huang, D. Vitharana, X. F. Zheng, L. Pu J. Am. Chem. Soc. 1997;119:12454-12464.
18. 12. Oligomers of 2,6-naphthodiol, see: G. H. Marin, V. Horak J. Org. Chem. 1994;59:4267-4271.
19. 4.