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Volumn , Issue 15, 2000, Pages 2689-2697

Glycine and alanine imines as templates for asymmetric synthesis of α-amino acids

Author keywords

Amino acids; Asymmetric synthesis; Imines; Schiff bases; , Didehydro amino acids

Indexed keywords

ALANINE DERIVATIVE; ALPHA AMINO ACID; GLYCINE DERIVATIVE; IMINE; OXAZINE DERIVATIVE; PYRAZINE DERIVATIVE; SCHIFF BASE;

EID: 0033859136     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200008)2000:15<2689::AID-EJOC2689>3.0.CO;2-T     Document Type: Short Survey
Times cited : (101)

References (110)
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    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1993) Tetrahedron , vol.49 , pp. 6515-6520
    • Anand, R.C.1    Singh, V.2
  • 59
    • 0028237841 scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5051-5054
    • Cardillo, G.1    De Simone, A.2    Gentilucci, L.3    Sabatino, P.4    Tomasini, C.5
  • 60
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    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1821-1824
    • Van Heerden, P.S.1    Bezuidenhoudt, B.C.B.2    Ferreira, D.3
  • 61
    • 0001447815 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1997) J. Org. Chem. , vol.62 , pp. 9148-9153
    • Bongini, A.1    Cardillo, G.2    Gentilucci, L.3    Tomasini, C.4
  • 62
    • 0030804229 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1486-1489
    • Trost, B.M.1    Ceschi, M.A.2    König, B.3
  • 63
    • 0032499048 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2203-2206
    • Caddick, S.1    Jenkins, K.2    Treweeke, N.3    Candeias, S.X.4    Afonso, C.A.M.5
  • 64
    • 0031688494 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1998) Synth. Commun. , vol.28 , pp. 3877-3884
    • Roos, G.H.P.1    Balasubramaniam, S.2
  • 65
    • 0000706732 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1999) Tetrahedron , vol.55 , pp. 3365-3376
    • Versttg, M.1
  • 66
    • 0033584983 scopus 로고    scopus 로고
    • For recent uses of this auxilary in asymmetric synthesis see for instance: [18a] K. N. Jenssen, G. H. P. Roos, Tetrahedron: Asymmetry 1992, 3, 1553-1554. [18b] O. Melnyk, E. Stephan, G. Pourcelot, P. Cresson, Tetrahedron 1992, 48, 841-850. [18c] S. E. Drewes, D. G. S. Malissar, G. H. P. Roos, Chem. Ber. 1993, 126, 2663-2673. [18d] R. C. Anand, V. Singh, Tetrahedron 1993, 49, 6515-6520. [18e] G. Cardillo, A. De Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett. 1994, 35, 5051-5054. [18f] P. S. Van Heerden, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron Lett. 1997, 38, 1821-1824. [18g] A. Bongini, G. Cardillo, L. Gentilucci, C. Tomasini, J. Org. Chem. 1997, 62, 9148-9153. [18h] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489. [18i] S. Caddick, K. Jenkins, N. Treweeke, S. X. Candeias, C. A. M. Afonso, Tetrahedron Lett. 1998, 39, 2203-2206. [18j] G. H. P. Roos, S. Balasubramaniam, Synth. Commun. 1998, 28, 3877-3884. [18k] M. Versttg, Tetrahedron 1999, 55, 3365-3376. [18l] G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261-8264.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8261-8264
    • Cardillo, G.1    Gentilucci, L.2    Tolomelli, A.3
  • 69
    • 0343042686 scopus 로고    scopus 로고
    • unpublished results
    • [19c] G. Guillena, unpublished results.
    • Guillena, G.1
  • 70
    • 0033152728 scopus 로고    scopus 로고
    • Highlights of this chemistry: A. Nelson, Angew. Chem. Int. Ed. 1999, 38, 1583-1585 and corrigendum in Angew. Chem. Int. Ed. 1999, 38, 3415.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1583-1585
    • Nelson, A.1
  • 71
    • 0033152728 scopus 로고    scopus 로고
    • Highlights of this chemistry: A. Nelson, Angew. Chem. Int. Ed. 1999, 38, 1583-1585 and corrigendum in Angew. Chem. Int. Ed. 1999, 38, 3415.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3415
  • 91
    • 0005324689 scopus 로고
    • To the best of our knowledge, the only example of this type of heterocycle is 1,2,3,6-tetrahydro-6,6-dimethyl-5-phenylpyrazinone which has been prepared by reaction of 2,2-dimethyl-3-phenyl-2H-azirine with glycine ethyl ester: G. Alvernhe, A. Laurent, A. Masroua, Tetrahedron Lett. 1983, 24, 1153-1156.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1153-1156
    • Alvernhe, G.1    Laurent, A.2    Masroua, A.3
  • 96
    • 0031983889 scopus 로고    scopus 로고
    • and references cited therein
    • J. Spengler, K. Burger, Synthesis 1998, 67-70 and references cited therein
    • (1998) Synthesis , pp. 67-70
    • Spengler, J.1    Burger, K.2
  • 97
    • 0343914282 scopus 로고    scopus 로고
    • Ph. D. Thesis, University of Alicante
    • N. Galindo, Ph. D. Thesis, University of Alicante, 1999.
    • (1999)
    • Galindo, N.1
  • 99
    • 0342608529 scopus 로고    scopus 로고
    • For recent reviews see refs. [1b, 1f]
    • For recent reviews see refs. [1b, 1f]
  • 106
    • 0343914279 scopus 로고    scopus 로고
    • The configuration of this cycloadduct could not be determined
    • The configuration of this cycloadduct could not be determined.
  • 110
    • 0342608524 scopus 로고    scopus 로고
    • note
    • LUMO = -0.33 eV (Hyperchem 5.0, from Hypercube, Inc.).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.