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Volumn 9, Issue 7, 1998, Pages 1125-1129

(4R,5S)-1,5-Dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative: Practical asymmetric synthesis of α-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIMETHYL 4 PHENYLIMIDAZOLIDIN 2 ONE; [BIS(METHYLTHIO)METHYLENE] GLYCINATE; ALPHA AMINO ACID; GLYCINE DERIVATIVE; HALIDE; IMIDAZOLIDINONE; UNCLASSIFIED DRUG;

EID: 0345294358     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00113-X     Document Type: Article
Times cited : (33)

References (35)
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    • (1994) Tetrahedron Lett. , vol.35 , pp. 5051-5054
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    • (1997) Tetrahedron Lett. , vol.38 , pp. 1821-1824
    • Van Heerden, P.S.1    Bezuidenhoudt, B.C.B.2    Ferreira, D.3
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    • 0001447815 scopus 로고    scopus 로고
    • See, for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Anand, R. C.; Singh, V. Tetrahedron 1993, 49, 6515-6520. (c) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (d) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (e) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (f) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (g) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. (h) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850.
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    • Bongini, A.1    Cardillo, G.2    Gentilucci, L.3    Tomasini, C.4
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    • See, for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Anand, R. C.; Singh, V. Tetrahedron 1993, 49, 6515-6520. (c) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (d) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (e) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (f) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (g) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. (h) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1553-1554
    • Jensen, K.N.1    Roos, G.H.P.2
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    • 0030804229 scopus 로고    scopus 로고
    • See, for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Anand, R. C.; Singh, V. Tetrahedron 1993, 49, 6515-6520. (c) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (d) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (e) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (f) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (g) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. (h) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1486-1489
    • Trost, B.M.1    Ceschi, M.A.2    König, B.3
  • 25
    • 0026584779 scopus 로고
    • See, for instance: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354-2356. (b) Anand, R. C.; Singh, V. Tetrahedron 1993, 49, 6515-6520. (c) Cardillo, G.; De Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051-5054. (d) van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 1821-1824. (e) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153. (f) Jensen, K. N.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 1553-1554. (g) Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. (h) Melnyk, O.; Stephan, E.; Pourcelot, G.; Cresson, P. Tetrahedron 1992, 48, 841-850.
    • (1992) Tetrahedron , vol.48 , pp. 841-850
    • Melnyk, O.1    Stephan, E.2    Pourcelot, G.3    Cresson, P.4
  • 29
    • 0344515671 scopus 로고    scopus 로고
    • note
    • 15 of imidazolidinone 8 with methyl N-[bis(methylthio)methylidene]glycinate gave very poor yields.
  • 34
    • 0344515670 scopus 로고    scopus 로고
    • note
    • This α-amino acid is very sensitive to hydrochloric acid.
  • 35
    • 0344946486 scopus 로고    scopus 로고
    • note
    • Ees were analyzed by HPLC using a Crownpak CR (+) column.


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