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Volumn 6, Issue 14, 2004, Pages 2397-2399

Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditions

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ETHER; ASPARTIC ACID; IMINO ACID; NITROGEN; SCHIFF BASE;

EID: 3242721636     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049215u     Document Type: Article
Times cited : (146)

References (29)
  • 1
    • 0002041453 scopus 로고    scopus 로고
    • Ojima, I., Ed.; Wiley-VCH: New York, Chapter 6A
    • For representative reviews, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6A, p 231. (b) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 231
    • Johnson, R.A.1    Sharpless, K.B.2
  • 2
    • 37649026114 scopus 로고    scopus 로고
    • For representative reviews, see: (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 6A, p 231. (b) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 92
    • Seebach, D.1    Beck, A.K.2    Heckel, A.3
  • 3
    • 0000125441 scopus 로고    scopus 로고
    • Reviews: (a) Sundquist, W. I.; Lippard, S. J. Coord. Chem. Rev. 1990, 100, 293. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2581. See also: Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barret, G. C., Ed.; Chapman and Hall: London, 1985; Chapter 4.
    • (1990) Coord. Chem. Rev. , vol.100 , pp. 293
    • Sundquist, W.I.1    Lippard, S.J.2
  • 4
    • 0000125441 scopus 로고    scopus 로고
    • Reviews: (a) Sundquist, W. I.; Lippard, S. J. Coord. Chem. Rev. 1990, 100, 293. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2581. See also: Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barret, G. C., Ed.; Chapman and Hall: London, 1985; Chapter 4.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2581
    • Lucet, D.1    Le Gall, T.2    Mioskowski, C.3
  • 5
    • 0000125441 scopus 로고    scopus 로고
    • Barret, G. C., Ed.; Chapman and Hall: London, Chapter 4
    • Reviews: (a) Sundquist, W. I.; Lippard, S. J. Coord. Chem. Rev. 1990, 100, 293. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2581. See also: (c) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barret, G. C., Ed.; Chapman and Hall: London, 1985; Chapter 4.
    • (1985) Chemistry and Biochemistry of the Amino Acids
    • Hunt, S.1
  • 12
    • 0001391862 scopus 로고    scopus 로고
    • See also: (b) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273. Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
    • (2001) Org. Lett. , vol.3 , pp. 1273
    • Ooi, T.1    Doda, K.2    Maruoka, K.3
  • 13
    • 0037011290 scopus 로고    scopus 로고
    • See also: (b) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273. (c) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4542
    • Ooi, T.1    Taniguchi, M.2    Kameda, M.3    Maruoka, K.4
  • 14
    • 0037473547 scopus 로고    scopus 로고
    • See also: (b) Ooi, T.; Doda, K.; Maruoka, K. Org. Lett. 2001, 3, 1273. (c) Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 4542. (d) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 5139
    • Ooi, T.1    Kameda, M.2    Maruoka, K.3
  • 15
    • 3242733154 scopus 로고    scopus 로고
    • note
    • 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.
  • 16
    • 0343907301 scopus 로고    scopus 로고
    • 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.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 673
    • Fernández-Megía, E.1    Sardina, F.J.2
  • 17
    • 0343219772 scopus 로고    scopus 로고
    • 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.
    • (1997) J. Org. Chem. , vol.62 , pp. 4770
    • Fernández-Megía, E.1    Iglesias-Pintos, J.M.2    Sardina, F.J.3
  • 18
    • 0016372792 scopus 로고
    • 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.
    • (1974) Tetrahedron Lett. , pp. 1413
    • Goto, T.1    Ohgi, T.2
  • 19
    • 0016373629 scopus 로고
    • 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.
    • (1974) Tetrahedron Lett. , pp. 1417
    • Kusumoto, S.1    Tsuji, S.2    Shiba, T.3
  • 20
    • 0016166455 scopus 로고
    • 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.
    • (1974) Bull. Chem. Soc. Jpn. , vol.47 , pp. 2690
    • Kusumoto, S.1    Tsuji, S.2    Shiba, T.3
  • 21
    • 0017030857 scopus 로고
    • 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.
    • (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 3611
    • Kusumoto, S.1    Tsuji, S.2    Shima, K.3    Shiba, T.4


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