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Volumn 79, Issue 7, 2006, Pages 1069-1083

Asymmetric 1,3-dipolar cycloaddition of nitrones with an electron-withdrawing group to allylic alcohols utilizing diisopropyl tartrate as a chiral auxiliary

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITY; ISOXAZOLIDINES; NITRONES;

EID: 33750576560     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.1069     Document Type: Article
Times cited : (21)

References (68)
  • 1
    • 0004136903 scopus 로고
    • ed. by D. P. Curran, Jai Press Inc., Greenwich
    • a) Advances in Cycloaddition, ed. by D. P. Curran, Jai Press Inc., Greenwich, 1988, Vol. 1;
    • (1988) Advances in Cycloaddition , vol.1
  • 5
    • 0000097153 scopus 로고    scopus 로고
    • ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, Chap. 33.1
    • b) D. A. Evans, J. S. Johnson, Comprehensive Asymmetric Catalysis, ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 1999, Chap. 33.1.
    • (1999) Comprehensive Asymmetric Catalysis
    • Evans, D.A.1    Johnson, J.S.2
  • 6
    • 38349191772 scopus 로고    scopus 로고
    • ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, Chap. 33.2
    • c) T. Ooi, K. Maruoka, Comprehensive Asymmetric Catalysis, ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 1999, Chap. 33.2.
    • (1999) Comprehensive Asymmetric Catalysis
    • Ooi, T.1    Maruoka, K.2
  • 7
  • 44
    • 0027398063 scopus 로고
    • See
    • Magnesium-mediated 1,3-dipolar cycloaddition of nitrones to 2-propen-1-ol was reported to give the corresponding cis-isoxazolidines diastereoselectively. The present our result that 2a and 2b diastereoselectively afforded the trans-isoxazolidines 4Aa and 4Ab, respectively, showed the opposite diastereoselection. See: a) S. Kanemasa, T. Tsuruoka, E. Wada, Tetrahedron Lett. 1993, 34, 87.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 87
    • Kanemasa, S.1    Tsuruoka, T.2    Wada, E.3
  • 48
    • 33750585311 scopus 로고    scopus 로고
    • note
    • 19 On the other hand, the equilibrium was established within 15 min at 50°C. These observations indicate at least that Z-2b was smoothly supplied at higher temperature via isomerizaion of E-2b when Z-2b was consumed by the 1,3-dipolar cycloaddition through the endo-transition state as shown in Fig. 4.
  • 49
    • 33750597111 scopus 로고    scopus 로고
    • note
    • The reaction using a N,N-dimethylamide-substituted nitrone instead of the N,N-dibenzylamide-substituted nitrone 2c or N,N-diisopropylamide-substituted nitrone 2d also gave the corresponding 3,5-cis-isoxazolidine diastereoselectively in 32% yield with the enantioselectivity of 61% ee under the same reaction conditions of Entry 1 in Table 2, which might imply that even the N,N-dimethylamide moiety is bulky enough to avoid the chelation to zinc metal to be subject to the exo-transition state in Fig. 5.
  • 64
    • 0002754809 scopus 로고
    • The stereochemistry of the obtained nitrone 2b was assigned based on the reported data of α-alkoxycarbonyl-N-alkylnitrones: a) Y. Inouye, J. Hara, H. Kakisawa, Chem. Lett. 1980, 1407.
    • (1980) Chem. Lett. , pp. 1407
    • Inouye, Y.1    Hara, J.2    Kakisawa, H.3
  • 66
    • 33750577552 scopus 로고    scopus 로고
    • note
    • During the optimization for the catalytic reaction, a small amount of 4Ac was obtained by chance using N-methylmorpholine N-oxide as an additive instead of pyridine N-oxide. By the racemic reaction promoted by magnesium, the trans-isoxazoline 4Ac was not obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.