메뉴 건너뛰기




Volumn 118, Issue 27, 1996, Pages 6520-6521

On the question of asymmetric induction with acyclic allylic substrates. An asymmetric synthesis of (+)-polyoxamic acid

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; POLYOL; POLYOXAMIC ACID; UNCLASSIFIED DRUG;

EID: 0029928975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961061t     Document Type: Article
Times cited : (153)

References (34)
  • 1
    • 6844254916 scopus 로고    scopus 로고
    • Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: Weinheim, 1993; pp 326-365.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, B.M.1    Van Vranken, D.L.2
  • 2
    • 8944232191 scopus 로고
    • Ojima, I., Ed.; VCH: Weinheim
    • Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Hayashi, T. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: Weinheim, 1993; pp 326-365.
    • (1993) Catalytic Asymmetric Synthesis , pp. 326-365
    • Hayashi, T.1
  • 4
    • 33748227479 scopus 로고
    • von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 566
    • Von Matt, P.1    Pfaltz, A.2
  • 5
    • 0027407117 scopus 로고
    • von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1769
    • Sprinz, J.1    Helmchen, G.2
  • 8
    • 0028948731 scopus 로고
    • von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron: Asymmetry 1994, 5, 573. Eichelmann, H.; Gais, H.-J. Tetrahedron: Asymmetry 1995, 6, 643.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 643
    • Eichelmann, H.1    Gais, H.-J.2
  • 13
    • 0039802579 scopus 로고
    • Schulte-Elte, K. H.; Willhalm, B.; Ohloff, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 985. Adams, W. R.; Trecker, D. J. Tetrahedron 1971, 27, 2631. Buendia, J.; Nierat, J.; Vivat, M. Bull. Soc. Chim. Fr II 1979, 46, 614.
    • (1971) Tetrahedron , vol.27 , pp. 2631
    • Adams, W.R.1    Trecker, D.J.2
  • 14
    • 0018614167 scopus 로고
    • Schulte-Elte, K. H.; Willhalm, B.; Ohloff, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 985. Adams, W. R.; Trecker, D. J. Tetrahedron 1971, 27, 2631. Buendia, J.; Nierat, J.; Vivat, M. Bull. Soc. Chim. Fr II 1979, 46, 614.
    • (1979) Bull. Soc. Chim. Fr II , vol.46 , pp. 614
    • Buendia, J.1    Nierat, J.2    Vivat, M.3
  • 17
    • 8944245940 scopus 로고    scopus 로고
    • note
    • 2). A plot of rotation vs ee for a series of samples of varying ee gave a straight line that indicates the maximum rotation is +34°.
  • 18
    • 8944237587 scopus 로고    scopus 로고
    • note
    • All new compounds have been fully characterized spectrally, and elemental composition has been established by high-resolution mass spectroscopy and/or combustion analysis (see the supporting information).
  • 20
    • 8944253401 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the bis-O-methylmandelate ester.
  • 21
    • 8944262926 scopus 로고    scopus 로고
    • note
    • The absolute configuration was established by conversion of the phthalimide group to an O-methylmandelamide (see ref 11).
  • 22
    • 8944246872 scopus 로고    scopus 로고
    • note
    • The ee values of 88% and 89%, respectively, were obtained using succinimide.
  • 23
    • 0024209272 scopus 로고
    • For a review, see: Isono, K. J. Antibiotics 1988, 41, 1711.
    • (1988) J. Antibiotics , vol.41 , pp. 1711
    • Isono, K.1
  • 24
    • 0028806478 scopus 로고
    • For recent synthetic approaches and references to previous work, see: Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431. Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111. Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
    • (1995) J. Org. Chem. , vol.60 , pp. 6431
    • Jackson, R.F.W.1    Palmer, N.J.2    Wythes, M.J.3    Clegg, W.4    Elsegood, M.R.J.5
  • 25
    • 0000042166 scopus 로고
    • For recent synthetic approaches and references to previous work, see: Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431. Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111. Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
    • (1994) J. Org. Chem. , vol.59 , pp. 5139
    • Marshall, J.A.1    Seletsky, B.M.2    Coan, P.S.3
  • 26
    • 0027976912 scopus 로고
    • For recent synthetic approaches and references to previous work, see: Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431. Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111. Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 733
    • Matsuura, F.1    Hamada, Y.2    Shioiri, T.3
  • 27
    • 0027952674 scopus 로고
    • For recent synthetic approaches and references to previous work, see: Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431. Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111. Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 111
    • Chida, N.1    Koizumi, K.2    Kitada, Y.3    Yokoyama, C.4    Ogawa, S.5
  • 28
    • 0027200453 scopus 로고
    • For recent synthetic approaches and references to previous work, see: Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431. Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733. Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 111. Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5479
    • Dondoni, A.1    Franco, S.2    Merchan, F.L.3    Merino, P.4    Tejero, T.5
  • 31
    • 4444276636 scopus 로고
    • Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Use of the allylic p-methoxybenzoate decreased the diastereoselectivity; cf.: Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
    • (1994) Chem. Rev. , vol.94 , pp. 2483
    • Kolb, H.C.1    Van Nieuwenhze, M.S.2    Sharpless, K.B.3
  • 32
    • 0000711829 scopus 로고
    • Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Use of the allylic p-methoxybenzoate decreased the diastereoselectivity; cf.: Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10805
    • Corey, E.J.1    Guzman-Perez, A.2    Noe, M.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.