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Volumn 40, Issue 9, 1999, Pages 1705-1708

Novel C2 chiral diamine ligands derived from cyclic Troger bases

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE;

EID: 0033605354     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00032-5     Document Type: Article
Times cited : (34)

References (38)
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  • 2
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    • 1. Tröger, J. J. Prakt. Chem. 1887, 36, 225-245. For a short review, see: Bag, B. G. Curr. Sci. 1995, 68, 279-288.
    • (1995) Curr. Sci. , vol.68 , pp. 279-288
    • Bag, B.G.1
  • 16
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    • (b) Crossley, R.; Downing, A. P.; Nógrádi, M.; Braga de Oliveira, A.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin I 1973, 205-217. Actually, preparation of the optical active Tröger base has been achieved by taking advantage of the acid-catalyzed isomerization in the presence of 1,1′-binaphthalene-2,2′-diyl hydrogen phosphate: Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991; 56: 485-487. One way to solve the racemization problem is to replace the endomethylene bridge with an ethano bridge: Hamada, Y.; Mukai, S. Tetrahedron Asymmetry 1996, 7, 2671-2674.
    • (1973) J. Chem. Soc., Perkin I , pp. 205-217
    • Crossley, R.1    Downing, A.P.2    Nógrádi, M.3    Braga De Oliveira, A.4    Ollis, W.D.5    Sutherland, I.O.6
  • 17
    • 0000654981 scopus 로고
    • (b) Crossley, R.; Downing, A. P.; Nógrádi, M.; Braga de Oliveira, A.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin I 1973, 205-217. Actually, preparation of the optical active Tröger base has been achieved by taking advantage of the acid-catalyzed isomerization in the presence of 1,1′-binaphthalene-2,2′-diyl hydrogen phosphate: Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991; 56: 485-487. One way to solve the racemization problem is to replace the endomethylene bridge with an ethano bridge: Hamada, Y.; Mukai, S. Tetrahedron Asymmetry 1996, 7, 2671-2674.
    • (1991) J. Org. Chem. , vol.56 , pp. 485-487
    • Wilen, S.H.1    Qi, J.Z.2    Williard, P.G.3
  • 18
    • 0030248639 scopus 로고    scopus 로고
    • (b) Crossley, R.; Downing, A. P.; Nógrádi, M.; Braga de Oliveira, A.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin I 1973, 205-217. Actually, preparation of the optical active Tröger base has been achieved by taking advantage of the acid-catalyzed isomerization in the presence of 1,1′-binaphthalene-2,2′-diyl hydrogen phosphate: Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991; 56: 485-487. One way to solve the racemization problem is to replace the endomethylene bridge with an ethano bridge: Hamada, Y.; Mukai, S. Tetrahedron Asymmetry 1996, 7, 2671-2674.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 2671-2674
    • Hamada, Y.1    Mukai, S.2
  • 20
    • 0030855097 scopus 로고    scopus 로고
    • 11. Larger trögerophanes 2c-e have recently been synthesized by different routes: Manjula, A.; Nagarajan, M. Tetrahedron 1997, 53, 11859-11868.
    • (1997) Tetrahedron , vol.53 , pp. 11859-11868
    • Manjula, A.1    Nagarajan, M.2
  • 21
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    • 12. Without dioxane as a cosolvent, only 5% yield of N,N′'-dimethyl compound 3c was obtained from methylation of N-methyl compound 3b: Cooper, F. C.; Partridge, M. W. J. Chem. Soc. 1957, 2888-2893.
    • (1957) J. Chem. Soc. , pp. 2888-2893
    • Cooper, F.C.1    Partridge, M.W.2
  • 22
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    • 13. The structure of the open chain 3c in the solid state has been determined as a twisted conformation by X-ray crystallography: Prasad, S. M.; Narayan, S. P.; Mandal, D. K.; Gupta, S. C. Acta Cryst. C 1993, 49, 531-533. The preference for the twisted conformation is suggested by ab initio calculations (Gaussian 94, B3LYP/ 6-31G*): to be published.
    • (1993) Acta Cryst. C , vol.49 , pp. 531-533
    • Prasad, S.M.1    Narayan, S.P.2    Mandal, D.K.3    Gupta, S.C.4
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    • 16. Daicel Chemical Industries, Ltd. Developed by Okamoto and his coworkers: (a) Okamoto, Y.; Aburatani, R.; Hatada, K. J. Chromatogr. 1987, 389, 95-102.
    • (1987) J. Chromatogr. , vol.389 , pp. 95-102
    • Okamoto, Y.1    Aburatani, R.2    Hatada, K.3
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    • note
    • 24 -198.1° (c 0.7, EtOH).
  • 29
    • 0013571803 scopus 로고    scopus 로고
    • note
    • 2: orange-yellow prisms from nitromethane. The details of the X-ray structural analysis will be reported elsewhere.
  • 30
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    • f have been mediated by closely related ethylenediamine-based chiral ligands. (a) Nozaki, H; Aratani, T.; Toraya, T, and Noyori, R. Tetrahedron 1971, 27, 905-913, Okamoto, Y.; Suzuki, K.; Yuki, H. J. Polymer Sci. 1980, 18, 3041-3051.
    • (1971) Tetrahedron , vol.27 , pp. 905-913
    • Nozaki, H.1    Aratani, T.2    Toraya, T.3    Noyori, R.4
  • 31
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    • f have been mediated by closely related ethylenediamine-based chiral ligands. (a) Nozaki, H; Aratani, T.; Toraya, T, and Noyori, R. Tetrahedron 1971, 27, 905-913, Okamoto, Y.; Suzuki, K.; Yuki, H. J. Polymer Sci. 1980, 18, 3041-3051.
    • (1980) J. Polymer Sci. , vol.18 , pp. 3041-3051
    • Okamoto, Y.1    Suzuki, K.2    Yuki, H.3
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    • (b) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585-4586, Sato, D.; Kawasaki, H.; Shimada, I.; Arata, Y.; Okamura, K.; Date, T.; Koza, K. Tetrahedron 1997, 53, 7191-7200.
    • (1981) Am. Chem. Soc. , vol.103 , pp. 4585-4586
    • Mazaleyrat, J.-P.1    Cram, D.J.J.2
  • 38
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    • note
    • 5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.