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Volumn 67, Issue 20, 2002, Pages 6896-6901

Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC POTENTIALS;

EID: 0037019991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025832p     Document Type: Article
Times cited : (46)

References (97)
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    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1989) Tetrahedron , vol.45 , pp. 327-336
    • Fleet, G.W.J.1    Ramsden, N.G.2    Witty, D.R.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1989) Tetrahedron , vol.45 , pp. 319-326
    • Fleet, G.W.J.1    Ramsden, N.G.2    Witty, D.R.3
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    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1994) J. Org. Chem. , vol.59 , pp. 3175-3185
    • Baxter, E.W.1    Reitz, A.B.2
  • 24
    • 0013589759 scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2621-2623
    • Park, K.H.1    Yoon, Y.J.2    Lee, S.G.3
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    • 33748723128 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 741-746
    • Xu, Y.-M.1    Zhou, W.-S.2
  • 26
    • 0000929876 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1998) J. Org. Chem. , vol.63 , pp. 841-859
    • Wu, X.-D.1    Khim, S.-K.2    Zhang, X.3    Cederstrom, E.M.4    Mariano, P.S.5
  • 27
    • 0001381255 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1998) Synlett , pp. 105-114
    • Ciufolini, M.A.1    Hermann, C.Y.W.2    Dong, Q.3    Shimizu, T.4    Swaminathan, S.5    Xi, N.6
  • 28
    • 0033575495 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1999) Tetrahedron , vol.55 , pp. 8931-8952
    • Meyers, A.I.1    Andres, C.J.2    Resek, J.E.3    Woodall, C.C.4    McLaughlin, M.A.5    Lee, P.H.6    Price, D.A.7
  • 29
    • 0033575507 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5331-5332
    • Shirai, M.1    Okamoto, S.2    Sato, F.3
  • 30
    • 0033531159 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1999) Chem. Commun. , vol.7 , pp. 41-42
    • Asano, K.1    Hakogi, T.2    Iwama, S.3    Katsumura, S.4
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    • 0033575507 scopus 로고    scopus 로고
    • Selected synthesis of 1-deoxymannojirimycin: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1985, 26, 1123-1126. (b) Pederson, R. L.; Kim, M.-J.; Wong, C.-H. Tetrahedron Lett. 1988, 29, 4645-4648. (c) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336. (d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 319-326. (e) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185. (f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621-2623. (g) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741-746. (h) Wu, X.-D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841-859. (i) Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114. (j) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952. (k) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332. (m) Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. Chem. Commun. 1999, 7, 41-42. (n) Shirai, M.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5331-5332
    • Shirai, M.1    Okamoto, S.2    Sato, F.3
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