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0029129501
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The product 3b was optically active, although the configuration has not been determined. For discussion of the stereochemistry of the similar products to 3b in this type of aziridine ring opening, see: Davoli, P.; Forni, A.; Moretti, I.; Prati, F. Tetrahedron: Asymmetry 1995, 6, 2011.
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0346395921
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note
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1.2b
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14
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33748605775
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For reviews of aziridine chemistry, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
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For reviews of aziridine chemistry, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
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For reviews of aziridine chemistry, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
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0346395920
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note
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3 and lanthanide triflates.
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18
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85022373579
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For examples, see: (a) Styngach, E. P.; Kuchkova, K. I.; Efremova, T. M.; Semenov, A. A. Chem. Heterocyl. Comp. 1973, 1378; Chem. Abstr. 1974, 80, 70734. (b) Apparao, S.; Singh, G.; Ila, H.; Junjappa, H. Indian J. Chem., Sect. B 1984, 23, 15. (c) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564. (d) Legters, J.; Thijis, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16. (e) Legters, J.; Johanmes, G. H.; Thijis, L.; Zwanenburg, B. Recl. Tray. Chim. Pays-Bas 1992, 111, 59.
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For examples, see: (a) Styngach, E. P.; Kuchkova, K. I.; Efremova, T. M.; Semenov, A. A. Chem. Heterocyl. Comp. 1973, 1378; Chem. Abstr. 1974, 80, 70734. (b) Apparao, S.; Singh, G.; Ila, H.; Junjappa, H. Indian J. Chem., Sect. B 1984, 23, 15. (c) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564. (d) Legters, J.; Thijis, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16. (e) Legters, J.; Johanmes, G. H.; Thijis, L.; Zwanenburg, B. Recl. Tray. Chim. Pays-Bas 1992, 111, 59.
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For examples, see: (a) Styngach, E. P.; Kuchkova, K. I.; Efremova, T. M.; Semenov, A. A. Chem. Heterocyl. Comp. 1973, 1378; Chem. Abstr. 1974, 80, 70734. (b) Apparao, S.; Singh, G.; Ila, H.; Junjappa, H. Indian J. Chem., Sect. B 1984, 23, 15. (c) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564. (d) Legters, J.; Thijis, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16. (e) Legters, J.; Johanmes, G. H.; Thijis, L.; Zwanenburg, B. Recl. Tray. Chim. Pays-Bas 1992, 111, 59.
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For examples, see: (a) Styngach, E. P.; Kuchkova, K. I.; Efremova, T. M.; Semenov, A. A. Chem. Heterocyl. Comp. 1973, 1378; Chem. Abstr. 1974, 80, 70734. (b) Apparao, S.; Singh, G.; Ila, H.; Junjappa, H. Indian J. Chem., Sect. B 1984, 23, 15. (c) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564. (d) Legters, J.; Thijis, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 16. (e) Legters, J.; Johanmes, G. H.; Thijis, L.; Zwanenburg, B. Recl. Tray. Chim. Pays-Bas 1992, 111, 59.
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24
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0345764885
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-
note
-
As it turned out later, 2-methylindole(1) is the best suitable substrate for this type of coupling.
-
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25
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(a) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393.
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0347025979
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note
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3 purchased from Aldrich, TCI and Taiheiyo Kinzoku Corporation were examined.
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Kobayashi S., Hachiya I., Araki M., Ishitani H.; Tetrahedron Lett.; 1993, 34: 3755.
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We thank Dr. N. Nomura of Nagayo University for a valuable advice about this procedure: Nomura, N.; Taira, A.; Yomioka, T.; Okada, M. Maeromolecules 2000, 33, 1497.
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0028198078
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For theoretical treatment of this type of reaction: Dubois, L.; Mehta, A.; Tourette, E.; Dodd, R. H. J. Org. Chem. 1994, 59, 434.
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3, see: (a) Mataubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 44, 6379. (b) Meguro, M.; Asano, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395. (c) Meguro, M.; Yamamoto, Y. Heteroeyeles 1996, 43, 2473.
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3, see: (a) Mataubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 44, 6379. (b) Meguro, M.; Asano, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395. (c) Meguro, M.; Yamamoto, Y. Heteroeyeles 1996, 43, 2473.
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3, see: (a) Mataubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 44, 6379. (b) Meguro, M.; Asano, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395. (c) Meguro, M.; Yamamoto, Y. Heteroeyeles 1996, 43, 2473.
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0346395914
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note
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3-mediated coupling of indole 4 (see Table 2) with aziridine 2 gave 48% yield of 10 as a single product after 20 h at r.t., while the coupling of 4-chloroindole(7) was very sluggish and gave a complex mixture.
-
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38
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For another important methodology for a variety of optically active tryptophanes, see: Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
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41
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0347025978
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note
-
3 to synthesize the analogs of α-C-mannosyltryptophan such as galactosyl- and glucosyl-analogs will be reported elsewhere.
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43
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44
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0347656752
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note
-
The optical rotation of 10a depends on the solvent used for measurement.
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