F8BINOL, an electronically perturbed version of BINOL with remarkable configurational stability

Organic Letters

Volumn 2, Issue 1, 2000, Pages 41-44

  Yudin, Andrei K ^a   Martyn, L James P ^a   Pandiaraju, Subramanian ^a   Zheng, Juan ^a   Lough, Alan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001876268     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991244v     Document Type: Article

References (27)

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2. (a) Chan, A. S. C.; Zhang, F. Y.; Yip, C. W. J. Am. Chem. Soc. 1997, 119, 4080.
3. (b) Zhang, F. Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179.
4. Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223.
5. Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693.
6. (e) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
7. (f) Reetz, M. T.; Merk, C.; Naberfeld, G.; Rudolph, J.; Griebenow, N.; Goddard, R. Tetrahedron Lett. 1997, 38, 5273.
8. Smart, B. E. In Organofluorine compounds: Principles and Commercial Applications; Banks, R. E., Ed.; Plenum Press: New York, 1994; Chapter 3.
9. (a) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99 and references therein.
10. (b) Soloshonok, V. A. Enantiocontrolled Synthesis of Fluoroorganic Compounds; Wiley: New York, 1999.
11. García Martínez, A.; Osío Barcina, J.; de Fresno Cerezo, A.; Rivas, R. G. J. Am. Chem. Soc. 1998, 120, 673.
12. Tang, T.-H.; Nowakowska, M.; Guillet, J. E.; Csizmadia, I. G. J. Mol. Struct. 1991, 232, 133.
13. Gronowitz, S. Ark. Kemi 1958, 12, 239.
14. The side reaction between tetrafluorobenzyne (2 equiv) and sulfur to give octafluorodibenzothiophene accounts for the moderate yield.
15. Pummerer, R.; Prell, E.; Rieche, A. Ber. 1926, 59B, 2159.
16. For resolution of BINOL through separation of the bis[(-)-menthoxycarbonyl] derivatives, see: Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599.
17. Kyba, E. P.; Gokel, G. W.; de Jong, F.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Kaplan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4173.
18. Partial decomposition due to nucleophilic aromatic substitution of fluorines by hydroxyl groups was observed under these conditions: Yudin. A. K.; Martyn, L. J. P. Unpublished data.
19. o)]. Data were collected on a Nonius Kappa-CCD. Data were integrated and scaled using the Denzo-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307). The structure was solved and refined using SHELXTL V5.0. (Sheldrick, G. M. SHELXTL/PC V5.1 Users Manual (1997), Bruker Analytical X-ray Systems, Madison, WI) All non-hydrogen atoms were refined with anisotropic parameters. Hydrogen atoms were included in geometric positions and treated as riding atoms.
20. o)]. Data were collected on a Nonius Kappa-CCD. Data were integrated and scaled using the Denzo-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307). The structure was solved and refined using SHELXTL V5.0. (Sheldrick, G. M. SHELXTL/PC V5.1 Users Manual (1997), Bruker Analytical X-ray Systems, Madison, WI) All non-hydrogen atoms were refined with anisotropic parameters. Hydrogen atoms were included in geometric positions and treated as riding atoms.
21. o)]. Data were collected on a Nonius Kappa-CCD. Data were integrated and scaled using the Denzo-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307). The structure was solved and refined using SHELXTL V5.0. (Sheldrick, G. M. SHELXTL/PC V5.1 Users Manual (1997), Bruker Analytical X-ray Systems, Madison, WI) All non-hydrogen atoms were refined with anisotropic parameters. Hydrogen atoms were included in geometric positions and treated as riding atoms.
22. Toda, F.; Tanaka, K.; Miyamoto, H.; Koshima, H.; Miyahara, I.; Hirotsu, K. J. Chem. Soc., Perkin Trans. 2 1997, 1877.
23. 8BINOL (2.07V vs Ag/AgCl) is 0.6 V more positive than that of BINOL (1.47 V vs Ag/AgCl).
24. For studies related to electronic effects of substituents on chiral ligands in asymmetric catalysis, see: (a) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948.
25. (b) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
26. Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931.
27. Jendralla, H.; Li, C. H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297.