Application of the CD exciton chirality method to chiral 1,2-diamines. Use of C(2v)-symmetrical 2,3-naphthalenedicarboximido chromophore

Enantiomer

Volumn 3, Issue 2, 1998, Pages 197-202

  Watanabe, Masataka ^a   Abe, Tetsuya ^a   Fujii, Yuichi ^a   Harada, Nobuyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

2,3 naphthalenedicarboximido chromophore; Absolute configuration and conformation; Chiral 1,2 diamines; Exciton CD spectra; Exciton chirality

Indexed keywords

ACID ANHYDRIDE; DIAMINE DERIVATIVE;

ARTICLE; CHIRALITY; CHROMATOPHORE; PRIORITY JOURNAL;

GOSSYPIUM HIRSUTUM;

EID: 0031770346     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, California, and Oxford University Press, Oxford, 1983.
2. K. Nakanishi, N. Berova and R.W. Woody, Eds., Circular Dichroism, Principles and Applications, VCH Publishers, Inc., New York, 1994.
3. M. Kawai, U. Nagai and M. Katsumi, Tetrahedron Lett., 3165 (1975).
4. D. Gargiulo, F. Derguini, N. Berova, K. Nakanishi and N. Harada, J. Am. Chem. Soc., 113, 7046 (1991);
5. N. Berova, D. Gargiulo, F. Derguini, K. Nakanishi and N. Harada, J. Am. Chem. Soc., 115, 4769 (1993).
6. 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, 1994, Chapter 13, p. 379.
7. For example, although the CD spectra of bis(benzamide) and bis(p-methoxycinnamide) derivatives of trans-1,2-cyclohexanediamine (1S,2S)-(+)-1 exhibit exciton Cotton effects of positive chirality, that of a Schiff base derivative made from (1S,2S)-(+)-1 shows Cotton effects of negative exciton chirality [3,4].
8. Recently phthalimido and 2,3-naphthalenedicarboximido chromophores were used for determination of the absolute configuration of aminoalcohols and related compounds: F. Kazmierczak, K. Gawronska, U. Rychlewska and J. Gawronski, Tetrahedron: Asymmetry, 5, 527 (1994);
9. J. Gawronski, F. Kazmierczak, K. Gawronska, P. Skowronek, J. Waluk and J. Marczyk, Tetrahedron, 52, 13201 (1996)
10. J. Gawronski, M.D. Rozwadowska and F. Kazmierczak, Polish J. Chem., 68, 2279 (1994);
11. V. Dirsch, J. Frederico, N. Zhao, G. Cai, Y. Chen, S. Vunnam, J. Odingo, H. Pu, K. Nakanishi, N. Berova, D. Liotta, A. Bielawska and Y. Hannun, Tetrahedron Lett., 36, 4959 (1995);
12. A. Kawamura, N. Berova, V. Dirsch, A. Mangoni, K. Nakanishi, G. Schwartz, A. Bielawska, Y. Hannun and I. Kitagawa, Bioorganic & Medicinal Chemistry, 4, 1035 (1996).
13. 4: C, 75.94; H, 4.67; N, 5.90. Found: C, 75.91; H, 4.62; N, 5.85.
14. 4: C, 79.71; H, 4.22; N, 4.89. Found: C, 79.78; H, 4.24; N, 4.86.
15. 3) δ 1.73 (3 H, d, J = 7.3 Hz), 3.99 (1 H, dd, J = 14.0, 3.7 Hz), 4.52 (1 H, dd, J = 14.0, 9.8 Hz), 4.80 (1 H, qdd, J = 7.3, 9.8, 3.7 Hz), 7.65 (2 H, dd, J = 6.1, 3.4 Hz), 7.67 (2 H, dd, J = 6.1, 3.4 Hz), 7.97 (2 H, dd, J = 6.1, 3.4 Hz), 8.01 (2 H, dd, J = 6.1, 3.4 Hz), 8.22 (2 H, s), 8.26 (2 H, s).
16. 4: C, 77.63; H, 4.34; N, 5.49. Found: C, 77.85; H, 4.52; N, 5.47.
17. 3) δ 0.95 (3 H, d, J = 6.6 Hz), 0.98 (3 H, d, J = 6.6 Hz), 1.60 (1 H, m), 1.73 (1 H, ddd, J = 13.8, 9.0, 5.3 Hz), 2.42 (1 H, ddd, J = 13.8, 10.5, 4.9 Hz), 3.95 (1 H, dd, J = 13.9, 3.2 Hz), 4.53 (1 H, dd, J = 13.9, 10.1 Hz), 4.72 (1 H, m), 7.66 (4 H, m), 7.98 (2 H, dd, J = 6.1, 3.4 Hz), 8.01 (2 H, m), 8.21 (2 H, s), 8.26 (2 H, br s).
18. 3) δ 0.85 (3 H, t, J = 7.4 Hz), 1.12 (1 H, m), 1.28 (3 H, d, J = 6.6 Hz), 1.41 (1 H, m), 2.63 (1 H, m), 4.16 (1 H, dd, J = 13.9, 2.6 Hz), 4.30 (1 H, td, J = 10.4, 2.6 Hz), 4.54 (1 H, dd, J = 13.9, 10.4 Hz), 7.63 (2 H, dd, J = 6.3, 3.2 Hz), 7.67 (2 H, br s), 7.96 (2 H, dd, J = 6.3, 3.2 Hz), 8.01 (2 H, br s), 8.19 (2 H, s).
19. N. Harada, H.-Y. Li, N. Koumura, T. Abe, M. Watanabe and M. Hagiwara, Enantiomer (in press).