Conformational studies by dynamic NMR. 93. Stereomutation, enantioseparation, and absolute configuration of the atropisomers of diarylbicyclononanes

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1815-1820

  Casarini, Daniele ^a   Rosini, Carlo ^a   Grilli, Stefano ^b   Lunazzi, Lodovico ^b   Mazzanti, Andrea ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SOLUTIONS; X RAY DIFFRACTION ANALYSIS;

STEREOMUTATION;

BENZENE;

9 (4 METHOXYPHENYL) 9 (1 NAPHTHYL)BICYCLO[3.3.1]NONANE; 9 (4 METHOXYPHENYL) 9 (3 METHYLPHENYL)BICYCLO[3.3.1]NONANE; BICYCLO COMPOUND; BICYCLONONANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATION; SEPARATION TECHNIQUE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

EID: 0037424483     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0265378     Document Type: Article

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23. 1H methoxy signal (DPFGSE-NOE sequence) and observing the positive NOE experienced by the hydrogens in the ortho position. The line of the corresponding carbons was then identified by means of a heteronuclear two-dimensional correlation (gHSQC sequence).
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27. Assignment of ref 9 indicates that the shift of the two carbons in position ortho to the methoxy group is about 113 ppm: as a consequence, the other aryl CH line, corresponding to a pair of equivalent carbons, had to be assigned to the meta carbons (shift at about 128 ppm).
28. The lower barrier observed for the rotation of the 4-methoxyphenyl group in 2 and 3 with respect to 1 (see Table 1) may be a consequence of an increase in the energy of the ground state because of the molecular crowding.
29. Contrary to the case of the unhindered compound 1, we were unable to grow single crystals appropriate for X-ray diffraction in the case of the hindered derivatives 2 and 3 (i.e., the compounds displaying atropisomerism at ambient temperature). Thus, even if we had had introduced a heavy atom into compound 3, we would have been quite unlikely to obtain crystals suitable for X-ray diffraction.
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31. Harada, N.; Chen, S. L.; Nakanishi, K. J. Am. Chem. Soc. 1975, 97, 5345. Harada, N.; Takuma, Y.; Uda, H. J. Am. Chem. Soc. 1976, 98, 5408. Harada, N.; Uda, K. J. Am. Chem. Soc. 1978, 100, 8022. Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H. J. Am. Chem. Soc. 1981, 103, 5590. Liu, H.; Nakanishi, K. J. Am. Chem. Soc. 1982, 104, 1178. Casarini, D.; Lunazzi, L.; Pasquali, F.; Gasparrini, F.; Villani, C. J. Am. Chem. Soc. 1992, 114, 6521. Zhao, N.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 1995, 117, 7844. Zahan, S.; Canary, J. W. Org. Lett. 1999, 1, 891.
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36. Harada, N.; Chen, S. L.; Nakanishi, K. J. Am. Chem. Soc. 1975, 97, 5345. Harada, N.; Takuma, Y.; Uda, H. J. Am. Chem. Soc. 1976, 98, 5408. Harada, N.; Uda, K. J. Am. Chem. Soc. 1978, 100, 8022. Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H. J. Am. Chem. Soc. 1981, 103, 5590. Liu, H.; Nakanishi, K. J. Am. Chem. Soc. 1982, 104, 1178. Casarini, D.; Lunazzi, L.; Pasquali, F.; Gasparrini, F.; Villani, C. J. Am. Chem. Soc. 1992, 114, 6521. Zhao, N.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 1995, 117, 7844. Zahan, S.; Canary, J. W. Org. Lett. 1999, 1, 891.
37. Harada, N.; Chen, S. L.; Nakanishi, K. J. Am. Chem. Soc. 1975, 97, 5345. Harada, N.; Takuma, Y.; Uda, H. J. Am. Chem. Soc. 1976, 98, 5408. Harada, N.; Uda, K. J. Am. Chem. Soc. 1978, 100, 8022. Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H. J. Am. Chem. Soc. 1981, 103, 5590. Liu, H.; Nakanishi, K. J. Am. Chem. Soc. 1982, 104, 1178. Casarini, D.; Lunazzi, L.; Pasquali, F.; Gasparrini, F.; Villani, C. J. Am. Chem. Soc. 1992, 114, 6521. Zhao, N.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 1995, 117, 7844. Zahan, S.; Canary, J. W. Org. Lett. 1999, 1, 891.
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40. For a treatment of the exciton model and its applications to organic stereochemistry, see: Mason, S. F. Quart. Rev. 1963, 17, 20. Mason, S. F. In Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry; Snatzke, G., Ed; Wiley: London, 1967; Chapter 4, p 71. Gottarelli, S.; Mason, S. F.; Torre, G. J. Chem. Soc. B 1970, 349. Charney, E. In The Molecular Basis of Optical Activity, Optical Rotatory Dispersion and Circular Dichroism; Wiley: New York, 1979. Mason, F. S. Molecular Optical Activity and Chiral Discrimination; Cambridge University Press: Cambridge, 1982.
41. For a treatment of the exciton model and its applications to organic stereochemistry, see: Mason, S. F. Quart. Rev. 1963, 17, 20. Mason, S. F. In Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry; Snatzke, G., Ed; Wiley: London, 1967; Chapter 4, p 71. Gottarelli, S.; Mason, S. F.; Torre, G. J. Chem. Soc. B 1970, 349. Charney, E. In The Molecular Basis of Optical Activity, Optical Rotatory Dispersion and Circular Dichroism; Wiley: New York, 1979. Mason, F. S. Molecular Optical Activity and Chiral Discrimination; Cambridge University Press: Cambridge, 1982.
42. For a treatment of the exciton model and its applications to organic stereochemistry, see: Mason, S. F. Quart. Rev. 1963, 17, 20. Mason, S. F. In Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry; Snatzke, G., Ed; Wiley: London, 1967; Chapter 4, p 71. Gottarelli, S.; Mason, S. F.; Torre, G. J. Chem. Soc. B 1970, 349. Charney, E. In The Molecular Basis of Optical Activity, Optical Rotatory Dispersion and Circular Dichroism; Wiley: New York, 1979. Mason, F. S. Molecular Optical Activity and Chiral Discrimination; Cambridge University Press: Cambridge, 1982.
43. Harada, N.; Nakanishi, K. Acc. Chem. Res. 1972, 5, 257. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983. Nakanishi, K,; Berova, N. In Circular Dichroism: Principle and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds; VCH: New York, 2000; Chapter 12, p 337.
44. Harada, N.; Nakanishi, K. Acc. Chem. Res. 1972, 5, 257. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983. Nakanishi, K,; Berova, N. In Circular Dichroism: Principle and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds; VCH: New York, 2000; Chapter 12, p 337.
45. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983. Nakanishi, K,; Berova, N. In Circular Dichroism: Principle and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds; VCH: New York, 2000; Chapter 12, p 337.
46. Michl, J.; Thulsturp, E. W. Spectroscopy with Polarized Light; VCH: New York, 1986.
47. Absorption and CD data for such chromophore can be found in: Rosini, C.; Spada, G. P.; Proni, G.; Masiero, S.; Scamuzzi, S. J. Am. Chem. Soc. 1997, 109, 5506.
48. Sagiv, J. Tetrahedron 1977, 33, 2303.
49. Ar bond defines the helix axis. In 3a and 3b, the helix axis refers to the torsion angle between C9 and the α-carbon of the naphthyl substituent.
50. Martinez, A. G.; Barcina, J. O.; Cerezo, A. F.; Schlüter, A. D.; Frahn, J. Adv. Mater. 1999, 11, 27.
51. Brown, J. H.; Bushweller, C. H.; QCPE program no. 633; Indiana University, Bloomington, IN.