Synthesis and characterization of novel chiral 1,2-diamines derived from α-pinene

Chemistry Letters

Volumn 34, Issue 11, 2005, Pages 1476-1477

  Suzuki, Toshiaki ^a   Shibata, Akira ^a   Morohashi, Naoya ^a   Ohba, Yoshihiro ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544432330     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1476     Document Type: Article

References (13)

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5. Several analogues of 2,3-pinane diamine have been reported, see examples: a) O. V. Bakhvalov, D. V. Korchagina, Yu. V. Gatilov, and V. A. Barkhash, Russ. J. Org. Chem., 36, 1601 (2000).
6. b) S. V. Larionov, L. I. Myachina, Z. A. Savel'eva, L. A. Glinskaya, R. F. Klevtsova, L. A. Sheludyakova, A. V. Tkachev, and S. N. Bizyaev, Russ. J. Coord. Chem., 30, 837 (2004).
7. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K. S. Jeong, H. L. Kwong, K. Morikawa, Z. M. Wang, D. Q. Xu, and X. L. Zhang, J. Org. Chem., 57, 2768 (1992).
8. W. E. Fristad, T. A. Brandvold, J. R. Peterson, and S. R. Thompson, J. Org. Chem., 50, 3647 (1985).
9. 3) δ: 23.7, 25.6, 28.0, 29.8, 32.8, 38.7, 40.2, 52.4, 60.7, 68.5.
10. 3 and concentration. However, it was very difficult to separate 6 and monoazide compounds under the conditions, in which the conversion yield of 6 from 1 is low.
11. 3) δ: 24.1, 28.4, 29.8, 31.2, 39.4, 39.9, 40.8, 50.7, 55.0, 55.7.
12. Diamine 2b in EtOH was mixed with L-(+)-tartaric acid, and the mixture was refluxed for 30 min. The white precipitate was separated by filtration to give 2b·L-(+)-tartrate 1:1 complex (92%).
13. int = 0.077), 755 observed reflections (I > 3.00σ(I)), 202 parameters, R = 0.059, wR = 0.066, refined against \F\, GOF = 1.456. Crystallographic data for this crystal has been deposited with the Cambridge Crystallographic Date Centre as supplementary publication No. CCDC 263943. Copies of the data can be obtained free of charge (via http://www.ccdc.cam.ac.uk/conts/retrieving.html) on application to CCDC, 12, Union Road, Cambridge CB2 1EZ, UK (Fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).