(R)-6,6′-Bis(trifluoromethanesulfonyl)-2,2′-dihydroxy-1,1′-binaphthyl: a new ligand for asymmetric synthesis

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4125-4128

  Mouhtady, Omar ^a   Gaspard Iloughmane, Hafida ^a   Laporterie, André ^a   Roux, Christophe Le ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ZIRCONIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; MANNICH REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33646506378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.069     Document Type: Article

References (23)

1. Noyori R., Tomino I., and Tanimoto Y. J. Am. Chem. Soc. 101 (1979) 3129-3131
2. Chen Y., Yekta S., and Yudin A.K. Chem. Rev. 103 (2003) 3155-3211
3. Cook G.R., Kargbo R., and Maity B. Org. Lett. 7 (2005) 2767-2770
4. Ishitani H., Ueno M., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 8180-8186
5. Ueno M., Ishitani H., and Kobayashi S. Org. Lett. 4 (2002) 3395-3397
6. Goumont R., Kizilian E., Buncel E., and Terrier F. Org. Biomol. Chem. 1 (2003) 1741-1748
7. Goumont R., Faucher N., Moutiers G., Tordeux M., and Wakselman C. Synthesis (1997) 691-695
8. The synthesis of racemic 3,3′-trifluoromethanesulfonyl-2,2′-dihydroxy-1,1′-binaphthyl has been recently reported using the anionic thia-Fries rearrangement of 1,1′-bi-2,2′-naphthol bis(trifluoromethanesulfonate):. Charmant J.P.H., Dyke A.M., and Lloyd-Jones G.C. J. Chem. Soc. Chem. Commun. (2003) 380-381
9. Hendrickson J.B., and Bair K.W. J. Org. Chem. 42 (1977) 3875-3878
10. Singh R.P., Cao G., Kirchmeier R.L., and Shreeve J.M. J. Org. Chem. 64 (1999) 2873-2876
11. Creary X. J. Org. Chem. 45 (1980) 2727-2729
12. Pevere, V.; Quiclet-Sire, B.; Zard, S.; Bertrand F. PCT Int. WO 00/00467.
13. Hamada T., and Yonemitsu O. Synthesis (1986) 852-854
14. Hu Q.S., Vitharana D., Liu G., Jain V., Wagaman M.W., Zhang L., Lee T., and Pu L. Macromolecules 29 (1996) 1082-1084
15. 3) δ 13.8, 22.4, 25.3, 28.9, 31.1, 69.2, 116.5, 116.6, 118.8, 118.9, 121.6, 121.9, 126.6, 126.7, 126.8, 126.9, 128.8, 129.5, 132.3, 132.4, 136.6, 136.7, 138.7, 141.6, 158.1, 158.2.
16. Garlyauskajte R.Y., Sereda S.V., and Yagupolskii L.M. Tetrahedron 50 (1994) 6891-6906
17. 3) δ 103.3.
18. Movchun V.N., Kolomeitsev A.A., and Yagupolskii Y.L. J. Fluorine Chem. 70 (1995) 255-257
19. 3) δ -2.86.
20. Bhatt M.V., and Kulkarni S.U. Synthesis (1983) 249-282 and references cited
21. 3) δ -2.58.
22. The enantiomeric purity of 1 (>99% ee) was determined by analytical HPLC using a chiralpak AD column (eluant: hexane/isopropanol: 80/20). The absolute structure of 1 was definitively established by X-ray diffraction (structure not shown).
23. Yamashita Y., Ishitani H., Shimizu H., and Kobayashi S. J. Am. Chem. Soc. 124 (2002) 3292-3302