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Volumn 7, Issue 7, 2005, Pages 1431-1434

Highly exo-selective and enantioselective cycloaddition reactions of nitrones catalyzed by a chiral binaphthyldiimine-Ni(II) complex

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; IMINE; LEWIS ACID; NAPHTHYL GROUP; NICKEL COMPLEX; NITRONE DERIVATIVE; THIAZOLIDINE DERIVATIVE;

EID: 17444374300     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050397h     Document Type: Article
Times cited : (87)

References (34)
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    • For recent reviews, see: (a) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; John Wiley and Sons: Hoboken, NJ, 2003. (b) Gothelf, K. V.; Jørgensen K. A. Chem Commun. 2000, 1449. (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863. (d) Frederickson, M. Tetrahedron 1997, 53, 403. (e) 1,3-Dipolar Cycloaddition Chemistry; General heterocyclic chemistry series; Padwa, A., Ed.; John Wiley and Sons: New York, 1984; Vol. 2, pp 83-168.
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    • For reactions with α,β-unsaturated aldehyds, see: (a) Viton, F.; Bernardinelli, G.; Kündig, E. P. J. Am. Chem. Soc. 2002, 124, 4968. (b) Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457. (c) Shirahase, M.; Kamenasa, S.; Oderaotoshi, Y. Org. Lett. 2004, 6, 675. (d) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716.
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    • 0001660873 scopus 로고    scopus 로고
    • For reactions with α,β-unsaturated aldehyds, see: (a) Viton, F.; Bernardinelli, G.; Kündig, E. P. J. Am. Chem. Soc. 2002, 124, 4968. (b) Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457. (c) Shirahase, M.; Kamenasa, S.; Oderaotoshi, Y. Org. Lett. 2004, 6, 675. (d) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716.
    • (2002) Org. Lett. , vol.4 , pp. 2457
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    • 1642404440 scopus 로고    scopus 로고
    • For reactions with α,β-unsaturated aldehyds, see: (a) Viton, F.; Bernardinelli, G.; Kündig, E. P. J. Am. Chem. Soc. 2002, 124, 4968. (b) Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457. (c) Shirahase, M.; Kamenasa, S.; Oderaotoshi, Y. Org. Lett. 2004, 6, 675. (d) Carmona, D.; Lamata, M. P.; Viguri, F.; Rodriguez, R.; Oro, L. A.; Balana, A. I.; Lahoz, F. J.; Tejero, T.; Merino, P.; Franco, S.; Montesa, I. J. Am. Chem. Soc. 2004, 126, 2716.
    • (2004) Org. Lett. , vol.6 , pp. 675
    • Shirahase, M.1    Kamenasa, S.2    Oderaotoshi, Y.3
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    • note
    • For the reaction of 1d, decreasing the catalyst loading to 1 or 2 mol % (rt for 112 h) resulted in lower yields (36% and 50%, respectively) and enantioselectivity (62%ee and 83% ee, respectively), but with high exo-selectivity (95:5 and 97:3, respectively).
  • 32
    • 17444407734 scopus 로고    scopus 로고
    • note
    • 2 for 160 h, 0% yield. Reaction of 1a with 2d: reflux in toluene for 20 h, 0% yield.
  • 33
    • 17444389155 scopus 로고    scopus 로고
    • note
    • 10


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