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Volumn 133, Issue 22, 2011, Pages 8470-8473

Catalyst-controlled torquoselectivity switch in the 4π ring-opening reaction of 2-amino-2-azetines giving β-substituted α,β- unsaturated amidines

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Indexed keywords

STEREOCHEMISTRY;

EID: 79958003193     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202576e     Document Type: Article
Times cited : (51)

References (27)
  • 17
    • 0035812783 scopus 로고    scopus 로고
    • 4π Electrocyclic ring-opening of neutral 2-azetines has been studied with discussion of the torquoselectivity
    • 4π Electrocyclic ring-opening of neutral 2-azetines has been studied with discussion of the torquoselectivity: Walker, M. J.; Hietbrink, B. N.; Thomas, B. E., IV; Nakamura, K.; Kallel, E. A.; Houk, K. N. J. Org. Chem. 2001, 66, 6669-6672
    • (2001) J. Org. Chem. , vol.66 , pp. 6669-6672
    • Walker, M.J.1    Hietbrink, B.N.2    Thomas, B.E.I.V.3    Nakamura, K.4    Kallel, E.A.5    Houk, K.N.6
  • 20
    • 0029775846 scopus 로고    scopus 로고
    • Studies without discussion of the torquoselectivity
    • Studies without discussion of the torquoselectivity: Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7634-7635
    • Kai, H.1    Iwamoto, K.2    Chatani, N.3    Murai, S.4
  • 22
    • 0027533284 scopus 로고
    • Niwayama and Houk have reported that the torquoselectivity of 4π ring-opening of acetylcyclobuten was changed in the absence or presence of Lewis acid.
    • Niwayama and Houk have reported that the torquoselectivity of 4π ring-opening of acetylcyclobuten was changed in the absence or presence of Lewis acid. Niwayama, S.; Houk, K. N. Tetrahedron Lett. 1993, 34, 1251-1254
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1251-1254
    • Niwayama, S.1    Houk, K.N.2
  • 24
    • 1542554559 scopus 로고
    • For a review: see
    • For a review: see Seeman, J. I. Chem. Rev. 1983, 83, 83-134
    • (1983) Chem. Rev. , vol.83 , pp. 83-134
    • Seeman, J.I.1
  • 26
    • 79957987323 scopus 로고    scopus 로고
    • The electronic effect of the N - Ar of 4 on the torquoselectivity was also evaluated. See SI.
    • The electronic effect of the N-Ar of 4 on the torquoselectivity was also evaluated. See SI.
  • 27
    • 79957980915 scopus 로고    scopus 로고
    • ⧧are estimated to be 91: 9 and 11: 89 in the solvated and ionic pair models, respectively, at 25 °C.
    • ⧧are estimated to be 91: 9 and 11: 89 in the solvated and ionic pair models, respectively, at 25 °C.


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