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In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
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In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
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In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787. (b) D'Aniello, F.; Schoenfelder, A.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636. For related works. see: (c) Frantz. D. E.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. (d) Boyall, D.; Ĺpez, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236.
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A portion of this study was reported in a preliminary communication: Ohno, H.; Hamaguchi, H.; Tanaka, T. Org. Lett. 2001, 3, 2269-2271.
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0345826419
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note
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13b For details, see the Supporting Information.
-
-
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43
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0345826418
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note
-
For synthesis of bromoallenes 7g and 9g bearing a methyl group, see the Supporting Information.
-
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44
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0000596010
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For a methanesulfonic acid mediated ring-opening reaction of vinylaziridines, see: (a) Tamamura, H.; Yamashita, M.; Muramatsu, H.; Ohno, H.; Ibuka, T.; Otaka, A.; Fujii, N. Chem. Commun. 1997, 23, 2327-2328. (b) Tamamura, H.; Yamashita, M.; Nakajima, Y.; Sakano, K.; Otaka, A.; Ohno, H.; Ibuka, T.; Fujii, N. J. Chem. Soc., Perkin Trans. 1 1999, 2983-2996.
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33746385828
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For a methanesulfonic acid mediated ring-opening reaction of vinylaziridines, see: (a) Tamamura, H.; Yamashita, M.; Muramatsu, H.; Ohno, H.; Ibuka, T.; Otaka, A.; Fujii, N. Chem. Commun. 1997, 23, 2327-2328. (b) Tamamura, H.; Yamashita, M.; Nakajima, Y.; Sakano, K.; Otaka, A.; Ohno, H.; Ibuka, T.; Fujii, N. J. Chem. Soc., Perkin Trans. 1 1999, 2983-2996.
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See also ref 6a and b
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0347718190
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note
-
Although the 2,3-cis selective synthesis of 2-ethynylaziridines was possible by the treatment of bromoallenes with NaH/DMF for a prolonged reaction time, yields of the one-pot aziridination-equilibration reaction are unsatisfactory.
-
-
-
-
50
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0001219079
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-
The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
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Ibuka, T.1
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Tamamura, H.9
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Yamamoto, Y.11
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51
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0000831199
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The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
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Miwa, Y.8
Taga, T.9
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52
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33748720246
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-
The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
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The thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented in our previous study; see: (a) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999-1015. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982-2991. (c) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1998, 3703-3716. Ohno, H.; Toda, A.; Fujii, N.; Miwa, Y.; Taga, T.; Yamaoka, Y.; Osawa, E.; Ibuka, T. Tetrahedron Lett. 1999, 40, 1331-1334.
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Montgomery J.A., Jr.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Baboul, A.G.36
Stefanov, B.B.37
Liu, G.38
Liashenko, A.39
Piskorz, P.40
Komaromi, I.41
Gomperts, R.42
Martin, R.L.43
Fox, D.J.44
Keith, T.45
Al-Laham, M.A.46
Peng, C.Y.47
Nanayakkara, A.48
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Wong, M.W.53
Andres, J.L.54
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Replogle, E.S.57
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0346457465
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note
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The calculations at B3LYP/6-31G level gave similar energy differences [e.g., ΔG (trans-B-cis-B) = 3.92 kcal/mol, vs 4.35 kcal/mol] and similar transition structures with the ones at B3LYP/6-31+G(d). Compare cis-B1 in Figure 3 with cis-B in Figure 4.
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note
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For synthesis of the starting amino alcohols, see the Supporting Information of ref 7d.
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