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Volumn 65, Issue 6, 2000, Pages 1697-1701

Catalysis of a Diels-Alder reaction by amidinium ions

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; CATION; ESTRONE; GUANIDINE DERIVATIVE;

EID: 0034708422     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991372x     Document Type: Article
Times cited : (81)

References (33)
  • 3
    • 33748880183 scopus 로고
    • (b) Jubian, V.; Veronese, A.; Dixon, R. P.; Hamilton, A. D. Angew. Chem. 1995, 107, 1343; Angew. Chem., Int. Ed. Engl. 1995, 34, 1237.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1237
  • 7
  • 8
    • 0029799744 scopus 로고    scopus 로고
    • (a) Muche, M.-S.; Göbel, M. W. Angew. Chem. 1996, 108, 2263; Angew. Chem., Int. Ed. Engl. 1996, 35, 2126.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2126
  • 16
    • 33748221799 scopus 로고
    • (a) Lehr, S.; Schütz, K.; Bauch, M.; Göbel, M. W. Angew. Chem. 1994, 106, 1041; Angew. Chem., Int. Ed. Engl. 1994, 33, 984.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 984
  • 23
    • 0000565711 scopus 로고
    • Sodium tetrakis(3,5-bis(trifluoromethy])phenyl)borate: (a) Iwamoto, H.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1983, 24, 4703. (b) Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4703
    • Iwamoto, H.1    Sonoda, T.2    Kobayashi, H.3
  • 25
    • 0343011665 scopus 로고    scopus 로고
    • note
    • In our initial experiments, isolated yields of rac-8 and rac-9 were determined instead of reaction rates. In accordance with their tendency of ion pairing, 12b led to the lowest and 12d to the best yields. The tetrafluoroborate salt 12a was not sufficiently soluble to be tested.
  • 26
    • 0343011664 scopus 로고
    • Wiley: New York
    • Sprinzak, Y. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 91.
    • (1963) Organic Syntheses , vol.4 , pp. 91
    • Sprinzak, Y.1
  • 33
    • 0343011661 scopus 로고    scopus 로고
    • note
    • The observation of significant enantioselectivities gives further evidence that amidinium catalysis is due to complex formation of cation and dienophile. Chirality transfer from amidinium ions to cycloadduct 8 cannot be explained by simple acid catalysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.