Circular dichroism and absolute stereochemistry of [8]paracyclophane-10-carbonitrile and related compounds

Enantiomer

Volumn 5, Issue 1, 2000, Pages 139-144

  Nehira, Tatsuo ^a   Soutome, Tomomi ^a   Harada, Nobuyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

electron SCF CI DV MO method; 8 Paracyclophane 10 carbaldehyde; 8 Paracyclophane 10 methanol; Absolute stereochemistry; CD spectra; Chiral 8 paracyclophane 10 carbonitrile; Methyl 8 paracyclophane 10 carboxylate

Indexed keywords

CYANIDE; PARACYCLOPHANE DERIVATIVE;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; ELECTRON; PRIORITY JOURNAL; STEREOCHEMISTRY; THEORY; X RAY CRYSTALLOGRAPHY;

EID: 0034026464     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. N. Harada, T. Soutome, T. Nehira, H. Uda, S. Oi, A. Okamura and S. Miyano, J. Am. Chem. Soc., 1993, 115, 7547-7548.
2. (a) N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, and Oxford University Press: Oxford, 1983;
3. (b) K. Nakanishi and N. Berova, in K. Nakanishi, N. Berova and R.W. Woody (Eds.) Circular Dichroism-Principles and Applications; VCH Publishers, Inc.: New York, NY, 1994, pp. 361-398.
4. (a) N. Harada, in K. Nakanishi, N. Berova and R.W. Woody (Eds.) Circular Dichroism-Principles and Applications; VCH Publishers, Inc.: New York, NY, 1994, pp. 335-360;
5. (b) N. Harada, J. Kohori, H. Uda, K. Nakanishi and R. Takeda, J. Am. Chem. Soc., 1985, 107, 423-428;
6. (c) N. Harada, J. Kohori, H. Uda and K. Toriumi, J. Org. Chem., 1989, 54, 1820-1826;
7. (d) N. Harada, H. Uda, T. Nozoe, Y. Okamoto, H. Wakabayashi and S. Ishikawa, J. Am. Chem. Soc., 1987, 109, 1661-1665;
8. (e) M. Kobayashi, N. Shimizu, I. Kitagawa, Y. Kyogoku, N. Harada and H. Uda, Tetrahedron Lett., 1985, 26, 3833-3836;
9. (f) N. Harada, H. Uda, M. Kobayashi, N. Shimizu and I. Kitagawa, J. Am. Chem. Soc., 1989, 111, 5668-5674;
10. (g) N. Harada, T. Sugioka, Y. Ando, H. Uda and T. Kuriki, J. Am. Chem. Soc., 1988, 110, 8483-8487;
11. (h) N. Harada, T. Sugioka, H. Uda and T. Kuriki, J. Org. Chem., 1990, 55, 3158-3163;
12. (i) N. Harada, T. Sugioka, H. Uda, T. Kuriki, M. Kobayashi and I. Kitagawa, J. Org. Chem., 1994, 59, 6606-6613;
13. (j) N. Harada, T. Sugioka, T. Soutome, N. Hiyoshi, H. Uda and T. Kuriki, Tetrahedron: Asymmetry, 1995, 6, 375-376;
14. (k) N. Harada and T. Sugioka, Total synthesis and absolute stereochemistry of novel biologically active marine natural products of Halenaquinol family: theoretical studies of CD spectra, in A.U. Rahman (Ed.) Studies in Natural Products Chemistry; Elsevier Science Publishers; Amsterdam, Vol. 17, 1995; pp. 33-72,
15. (l) N. Harada, H. Ono, H. Uda, M. Parveen, N.U.-P. Khan, B. Achari and P.K. Dutta, J. Am. Chem. Soc., 1992, 114, 7687-7692;
16. (m) N. Harada, H.-Y. Li, T. Nehira and M. Hagiwara, Enantiomer, 1997, 2, 353-358;
17. (n) H.-Y. Li, T. Nehira, M. Hagiwara and N. Harada, J. Org. Chem., 1997, 62, 7222-7227;
18. (o) N. Harada, A. Saito, N. Koumura, H. Uda, B. de Lange, W.F. Jager, H. Wynberg and B.L. Feringa, J. Am. Chem. Soc., 1997, 119, 7241-7248;
19. (p) N. Harada, A. Saito, N. Koumura, D.C. Roe, W.F. Jager, R.W.J. Zijlstra, B. de Lange and B.L. Feringa, J. Am. Chem. Soc., 1997, 119, 7249-7255;
20. (q) N. Harada, N. Koumura and B.L. Feringa, J. Am. Chem. Soc., 1997, 119, 7256-7264;
21. (r) N. Koumura and N. Harada, Enantiomer, 1998, 3, 251-253;
22. (s) N. Koumura and N. Harada, Chem. Lett., 1998, 1151-1152;
23. (t) R.W.J. Zijlstra, W.F. Jager, B. de Lange, P.T. van Duijnen, B.L. Feringa, H. Goto, A. Saito, N. Koumura and N. Harada, J. Org. Chem., 1999, 64, 1667-1674.
24. V.V. Kane, W.H. De Wolf and F. Bickelhaupt, Tetrahedron, 1994, 50, 4575-4622.
25. The designation of enantiomers by CD data, see N. Harada, J. Iwabuchi, Y. Yokota, H. Uda, Y. Okamoto, H. Yuki and Y. Kawada, J. Chem. Soc., Perkin. Trans. I, 1985, 1845-1848; N. Harada, Enantiomer, 1996, 1, 81-82.
26. The designation of enantiomers by CD data, see N. Harada, J. Iwabuchi, Y. Yokota, H. Uda, Y. Okamoto, H. Yuki and Y. Kawada, J. Chem. Soc., Perkin. Trans. I, 1985, 1845-1848; N. Harada, Enantiomer, 1996, 1, 81-82.
27. 22O: C, 82.52; H, 10.16. Found: C, 82.79; H, 10.22.
28. 2: C, 78.01; H, 9.00. Found: C, 78.23; H, 9.21.
29. 3) δ -0.63 (1H, m), 0.10-1.98 (11H, m), 2.49 (1H, ddd, J = 13.1, 10.3, 5.3 Hz), 2.73 (2H, br t, J = 6.1 Hz), 3.79 (1H, ddd, J = 13.1, 4.7, 4.7 Hz), 7.20 (1H, d, J = 7.9 Hz), 7.39 (1H, dd, J = 7.9, 1.8 Hz), 7.72 (1H, d, J = 1.8 Hz), 10.26 (1H, s).
30. 19N: C, 84.45; H, 8.98; N, 6.57. Found: C, 84.54; H, 9.08; N, 6.47.
31. See Refs. [2a,3a,k].
32. N. Harada, CD & UV program, CD/NH-Sendai, 1975.