메뉴 건너뛰기




Volumn 59, Issue 49, 2003, Pages 9803-9810

A new synthesis of enantiomerically pure α- and β-amino acid derivatives using aziridinyl anions

Author keywords

Aziridinyllithium; Aziridinylmagnesium; Chiral synthesis; Sulfoxide metal exchange; amino acid; amino acid

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; ANION; AZIRIDINE DERIVATIVE; BETA AMINO ACID; BROMINE DERIVATIVE; DEUTERIUM; ETHYLMAGNESIUM BROMIDE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; NITROGEN; TERT BUTYLLITHIUM; UNCLASSIFIED DRUG;

EID: 0242558390     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.025     Document Type: Article
Times cited : (41)

References (39)
  • 1
    • 0003828324 scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (1985) Chemistry and Biochemistry of the Amino Acids
    • Williams, R.M.1
  • 2
    • 0003416748 scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (1989) Synthesis of Optically Active α-Amino Acids
  • 3
    • 0028355337 scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (1994) Tetrahedron , vol.50 , pp. 1539
    • Duthaler, R.O.1
  • 4
    • 0032561221 scopus 로고    scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3517
    • Cativiela, C.1    Diaz-De-Villegas, M.D.2
  • 5
    • 0033967405 scopus 로고    scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (2000) Yakugaku Zasshi , vol.120 , pp. 28
    • Sano, S.1
  • 6
    • 0011189302 scopus 로고    scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (2000) J. Synth. Org. Chem. Jpn , vol.58 , pp. 756
    • Sano, S.1    Nagao, Y.2
  • 7
    • 0034712270 scopus 로고    scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 645
    • Cativiela, C.1    Diaz-De-Villegas, M.D.2
  • 8
    • 0034677864 scopus 로고    scopus 로고
    • Recent monographs and reviews for the chemistry and synthesis of α-amino acids: (a) Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman & Hall, London, Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford, Duthaler R.O. Tetrahedron. 50:1994;1539 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517 Sano S. Yakugaku Zasshi. 120:2000;28 Sano S., Nagao Y. J. Synth. Org. Chem. Jpn. 58:2000;756 Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 11:2000;645 Beller M., Eckert M. Angew. Chem. Int. Ed. 39:2000;1010.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1010
    • Beller, M.1    Eckert, M.2
  • 9
    • 0028130028 scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (1994) Tetrahedron , vol.50 , pp. 9517
    • Cole, D.C.1
  • 10
    • 0002497398 scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (1994) Aldrichim. Acta , vol.27 , pp. 3
    • Juaristi, E.1    Quintana, D.2    Escalante, J.3
  • 11
    • 0003693460 scopus 로고    scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (1997) Enantioselective Synthesis of β-Amino Acids
    • Davies, S.G.1    Ichihara, O.2
  • 12
    • 0242508090 scopus 로고    scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (1997) J. Synth. Org. Chem. Jpn , vol.55 , pp. 26
  • 13
    • 0035215545 scopus 로고    scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (2001) Synlett , pp. 1813
    • Palomo, C.1    Aizpurua, J.M.2    Ganboa, I.3    Oiarbide, M.4
  • 14
    • 0037201534 scopus 로고    scopus 로고
    • Recent monograph and reviews for the chemistry and synthesis of β-amino acids: (a) Cole D.C. Tetrahedron. 50:1994;9517 Juaristi E., Quintana D., Escalante J. Aldrichim. Acta. 27:1994;3 Juaristi E. Enantioselective Synthesis of β-Amino Acids. 1997;Wiley-VCH, New York, Davies S.G., Ichihara O. J. Synth. Org. Chem. Jpn. 55:1997;26 Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813 Liu M., Sibi M.P. Tetrahedron. 58:2002;7991.
    • (2002) Tetrahedron , vol.58 , pp. 7991
    • Liu, M.1    Sibi, M.P.2
  • 15
    • 0000449913 scopus 로고
    • Martin S.F. Tetrahedron. 36:1980;419 Fuji K. Chem. Rev. 93:1993;2037 Corey E.J., Guzman-Perez A. Angew Chem. Int. Ed. 37:1998;388.
    • (1980) Tetrahedron , vol.36 , pp. 419
    • Martin, S.F.1
  • 16
    • 0001521888 scopus 로고
    • Martin S.F. Tetrahedron. 36:1980;419 Fuji K. Chem. Rev. 93:1993;2037 Corey E.J., Guzman-Perez A. Angew Chem. Int. Ed. 37:1998;388.
    • (1993) Chem. Rev. , vol.93 , pp. 2037
    • Fuji, K.1
  • 19
    • 0000027063 scopus 로고
    • Satoh T., Oohara T., Yamakawa K. Tetrahedron Lett. 29:1988;4093 Satoh T., Sato T., Oohara T., Yamakawa K. J. Org. Chem. 54:1989;3973 Satoh T. J. Synth. Org. Chem. Jpn. 54:1996;481 Satoh T. J. Synth. Org. Chem. Jpn. 61:2003;98.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4093
    • Satoh, T.1    Oohara, T.2    Yamakawa, K.3
  • 20
    • 0000730434 scopus 로고
    • Satoh T., Oohara T., Yamakawa K. Tetrahedron Lett. 29:1988;4093 Satoh T., Sato T., Oohara T., Yamakawa K. J. Org. Chem. 54:1989;3973 Satoh T. J. Synth. Org. Chem. Jpn. 54:1996;481 Satoh T. J. Synth. Org. Chem. Jpn. 61:2003;98.
    • (1989) J. Org. Chem. , vol.54 , pp. 3973
    • Satoh, T.1    Sato, T.2    Oohara, T.3    Yamakawa, K.4
  • 21
    • 0030165216 scopus 로고    scopus 로고
    • Satoh T., Oohara T., Yamakawa K. Tetrahedron Lett. 29:1988;4093 Satoh T., Sato T., Oohara T., Yamakawa K. J. Org. Chem. 54:1989;3973 Satoh T. J. Synth. Org. Chem. Jpn. 54:1996;481 Satoh T. J. Synth. Org. Chem. Jpn. 61:2003;98.
    • (1996) J. Synth. Org. Chem. Jpn , vol.54 , pp. 481
    • Satoh, T.1
  • 22
    • 0037667764 scopus 로고    scopus 로고
    • Satoh T., Oohara T., Yamakawa K. Tetrahedron Lett. 29:1988;4093 Satoh T., Sato T., Oohara T., Yamakawa K. J. Org. Chem. 54:1989;3973 Satoh T. J. Synth. Org. Chem. Jpn. 54:1996;481 Satoh T. J. Synth. Org. Chem. Jpn. 61:2003;98.
    • (2003) J. Synth. Org. Chem. Jpn , vol.61 , pp. 98
    • Satoh, T.1
  • 23
    • 0032537205 scopus 로고    scopus 로고
    • Satoh T., Ozawa M., Takano K., Kudo M. Tetrahedron Lett. 39:1998;2345 Satoh T., Ozawa M., Takano K., Chyouma T., Okawa A. Tetrahedron. 56:2000;4415 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron Lett. 41:2000;6495 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron. 57:2001;3891.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2345
    • Satoh, T.1    Ozawa, M.2    Takano, K.3    Kudo, M.4
  • 24
    • 0034705509 scopus 로고    scopus 로고
    • Satoh T., Ozawa M., Takano K., Kudo M. Tetrahedron Lett. 39:1998;2345 Satoh T., Ozawa M., Takano K., Chyouma T., Okawa A. Tetrahedron. 56:2000;4415 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron Lett. 41:2000;6495 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron. 57:2001;3891.
    • (2000) Tetrahedron , vol.56 , pp. 4415
    • Satoh, T.1    Ozawa, M.2    Takano, K.3    Chyouma, T.4    Okawa, A.5
  • 25
    • 0034641504 scopus 로고    scopus 로고
    • Satoh T., Ozawa M., Takano K., Kudo M. Tetrahedron Lett. 39:1998;2345 Satoh T., Ozawa M., Takano K., Chyouma T., Okawa A. Tetrahedron. 56:2000;4415 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron Lett. 41:2000;6495 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron. 57:2001;3891.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6495
    • Satoh, T.1    Matsue, R.2    Fujii, T.3    Morikawa, S.4
  • 26
    • 0035971893 scopus 로고    scopus 로고
    • Satoh T., Ozawa M., Takano K., Kudo M. Tetrahedron Lett. 39:1998;2345 Satoh T., Ozawa M., Takano K., Chyouma T., Okawa A. Tetrahedron. 56:2000;4415 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron Lett. 41:2000;6495 Satoh T., Matsue R., Fujii T., Morikawa S. Tetrahedron. 57:2001;3891.
    • (2001) Tetrahedron , vol.57 , pp. 3891
    • Satoh, T.1    Matsue, R.2    Fujii, T.3    Morikawa, S.4
  • 27
    • 0030586111 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5179
    • Atkinson, R.S.1    Coogan, M.P.2    Lochrie, I.S.T.3
  • 28
    • 0030605852 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5473
    • Davis, F.A.1    Liu, H.2    Reddy, G.V.3
  • 29
    • 0032552213 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1997) J. Org. Chem. , vol.62 , pp. 743
    • Choi, S.-K.1    Lee, J.-S.2    Kim, J.-H.3    Lee, W.K.4
  • 30
    • 0030851227 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1997) J. Org. Chem. , vol.62 , pp. 3796
    • Davis, F.A.1    Liang, C.-H.2    Liu, H.3
  • 31
    • 0030886048 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1997) Tetrahedron , vol.53 , pp. 13603
    • Kim, D.Y.1    Rhie, D.Y.2
  • 32
    • 0032506575 scopus 로고    scopus 로고
    • Atkinson R.S., Coogan M.P., Lochrie I.S.T. Tetrahedron Lett. 37: 1996;5179 Davis F.A., Liu H., Reddy G.V. Tetrahedron Lett. 37:1996;5473 Choi S.-K., Lee J.-S., Kim J.-H., Lee W.K. J. Org. Chem. 62:1997;743 Davis F.A., Liang C.-H., Liu H. J. Org. Chem. 62:1997;3796 Kim D.Y., Rhie D.Y. Tetrahedron. 53:1997;13603 Chang J.-W., Bae J.-H., Shin S.-H., Park C.S., Choi D., Lee W.K. Tetrahedron Lett. 39:1998;9193.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9193
    • Chang, J.-W.1    Bae, J.-H.2    Shin, S.-H.3    Park, C.S.4    Choi, D.5    Lee, W.K.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.