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3242733154
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note
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Representative results of the Mannich reaction of 3 with NaOH aqueous solutions of different concentrations are as follows: 10% NaOH, 11% yield (syn/anti = 70:30), 77% ee (syn isomer); 25% NaOH, 43% yield (71:29), 78% ee; 50% NaOH, 81% yield (79:21), 6% ee.
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16
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0343907301
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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Sardina, F.J.2
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17
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0343219772
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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Sardina, F.J.3
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0016372792
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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Goto, T.1
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19
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. (d) Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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0016166455
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. (d) Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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For recent synthetic efforts using 3-aminoaspartate as a key intermediate, see: (a) Fernández-Megía, E.; Sardina, F. J. Tetrahedron Lett. 1997, 38, 673. (b) Fernández-Megía, E.; Iglesias-Pintos, J. M.; Sardina, F. J. J. Org. Chem. 1997, 62, 4770. From carbohydrates: (c) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413. (d) Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417. (e) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690. (f) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull Chem. Soc. Jpn. 1976, 49, 3611.
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