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Volumn 7, Issue 6, 2005, Pages 1023-1026

Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide lodo binaphtholates

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; CYCLOHEXENE DERIVATIVE; EPOXIDE; LANTHANIDE; SAMARIUM;

EID: 18344379719     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0475360     Document Type: Article
Times cited : (125)

References (53)
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    • For ring opening by silyl azide, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2765. (b) Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 6142. (c) McCleland, B. W.; Nugent, W. A.; Finn, M. G. J. Org. Chem. 1998, 63, 6656. (d) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (e) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924. For ring opening by trimethyl silyl cyanide, see: (f) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1997, 36, 1704. (g) Zhu, C.; Yuan, F.; Gu, W.; Pan, Y. Chem. Commun. 2003, 692.
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    • For ring opening by silyl azide, see: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2765. (b) Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1994, 116, 6142. (c) McCleland, B. W.; Nugent, W. A.; Finn, M. G. J. Org. Chem. 1998, 63, 6656. (d) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. (e) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924. For ring opening by trimethyl silyl cyanide, see: (f) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1997, 36, 1704. (g) Zhu, C.; Yuan, F.; Gu, W.; Pan, Y. Chem. Commun. 2003, 692.
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    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
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    • Iida, T.1    Yamamoto, N.2    Sasai, H.3    Shibasaki, M.4
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    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
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    • Matsunaga, S.1    Das, J.2    Roels, J.3    Vogl, E.M.4    Yamamoto, N.5    Iida, T.6    Yamaguchi, K.7    Shibasaki, M.8
  • 20
    • 0031704998 scopus 로고    scopus 로고
    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2223
    • Iida, T.1    Yamamoto, N.2    Mastunaga, S.3    Woo, H.G.4    Shibasaki, M.5
  • 21
    • 0032558670 scopus 로고    scopus 로고
    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7917
    • Vogl, E.M.1    Matsunaga, S.2    Kanai, M.3    Iida, T.4    Shibasaki, M.5
  • 22
    • 0031024261 scopus 로고    scopus 로고
    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
    • (1997) N. Tetrahedron Lett. , vol.38 , pp. 773
    • Jacobsen, E.1
  • 23
    • 33745830746 scopus 로고    scopus 로고
    • For ring opening by thiols or phenols, see: (a) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783. (b) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (c) Iida, T.; Yamamoto, N.; Mastunaga, S.; Woo, H. G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223. (d) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. For ring opening by acids: (e) Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 773. For ring opening by indoles, see: (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 84.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 84
    • Bandini, M.1    Cozzi, P.G.2    Melchiorre, P.3    Umani-Ronchi, A.4
  • 41
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    • During studies of Diels-Alder reactions, we observed that the presence of molecular sieves allowed improvement of the conversion without modification of the enantiomeric excess, and all our subsequent catalytic experiments have been performed with 4 Å molecular sieves
    • During studies of Diels-Alder reactions, we observed that the presence of molecular sieves allowed improvement of the conversion without modification of the enantiomeric excess, and all our subsequent catalytic experiments have been performed with 4 Å molecular sieves.


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