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Tröger, J.1
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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.
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3. (a) Cowart, M. D.; Sucholeiki, I.; Bukownik, R. R.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 6204-6210.
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5. Ibrahim, A. A.; Matsumoto, M.; Miyahara, Y.; Izumi, K.; Suenaga, M.; Shimizu, N.; Inazu, T. J. Heterocycl. Chem. 1998, 35, 209-215.
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8. (a) Hussain, M. S.; Rehman, S. Z. Naturforsch., Teil B 1978, 336, 67-74.
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9. (a) Greenberg, A.; Molinaro, N.; Lang, M. J. Org. Chem. 1984, 49, 1127-1130.
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37049135619
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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.
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Crossley, R.1
Downing, A.P.2
Nógrádi, M.3
Braga De Oliveira, A.4
Ollis, W.D.5
Sutherland, I.O.6
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17
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0000654981
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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.
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Wilen, S.H.1
Qi, J.Z.2
Williard, P.G.3
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18
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0030248639
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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.
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(1996)
Tetrahedron Asymmetry
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Hamada, Y.1
Mukai, S.2
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20
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0030855097
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11. Larger trögerophanes 2c-e have recently been synthesized by different routes: Manjula, A.; Nagarajan, M. Tetrahedron 1997, 53, 11859-11868.
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(1997)
Tetrahedron
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Manjula, A.1
Nagarajan, M.2
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21
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37049048023
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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.
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Cooper, F.C.1
Partridge, M.W.2
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22
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84988289873
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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.
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Acta Cryst. C
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Prasad, S.M.1
Narayan, S.P.2
Mandal, D.K.3
Gupta, S.C.4
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24
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0027339217
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(b) Johnson, R. A.; Gorman, R. R.; Wnuk, R.J.; Crittenden, N. J.; Aiken, J. W. J. Med. Chem. 1993, 36, 3202-3206.
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26
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0006598577
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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.
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Okamoto, Y.1
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28
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0013620645
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note
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24 -198.1° (c 0.7, EtOH).
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29
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0013571803
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note
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2: orange-yellow prisms from nitromethane. The details of the X-ray structural analysis will be reported elsewhere.
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30
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0001251122
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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.
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Nozaki, H.1
Aratani, T.2
Toraya, T.3
Noyori, R.4
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31
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0013571232
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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.
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Okamoto, Y.1
Suzuki, K.2
Yuki, H.3
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32
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33845557984
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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.
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Mazaleyrat, J.-P.1
Cram, D.J.J.2
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33
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0030915513
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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.
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Tetrahedron
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Sato, D.1
Kawasaki, H.2
Shimada, I.3
Arata, Y.4
Okamura, K.5
Date, T.6
Koza, K.7
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34
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0013571671
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(c) Tomioka, K.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1987, 28, 1291-1292,
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Tomioka, K.1
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Koga, K.3
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36
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0000858703
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(e) Kobayashi, S.; Uchino, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247-4252.
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37
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0027136718
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(f) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138.
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Kubota, H.1
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Koga, K.3
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38
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0013571456
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note
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