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Volumn 131, Issue 21, 2009, Pages 7242-7243

Chiral arylaminophosphonium barfates as a new class of charged Brønsted acid for the enantioselective activation of nonionic Lewis bases

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; ARYL AMINES; CHEMICAL EQUATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CONJUGATE ADDITION; LEWIS BASIS; MOLECULAR DESIGN; NEW CLASS; NITROOLEFINS; NONIONIC; STEREOCONTROLLING; SYNTHETIC UTILITY;

EID: 67650513901     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903271t     Document Type: Article
Times cited : (108)

References (49)
  • 1
    • 38349135345 scopus 로고    scopus 로고
    • For selected recent reviews on Brønsted acid catalysis, see
    • For selected recent reviews on Brønsted acid catalysis, see: (a) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
    • (2007) Chem. Rev. , vol.107 , pp. 5713
    • Doyle, A.G.1    Jacobsen, E.N.2
  • 4
    • 29844448114 scopus 로고    scopus 로고
    • Reviews on nonionic Brønsted acid catalysis using thiourea
    • Reviews on nonionic Brønsted acid catalysis using thiourea: (a) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 4299
    • Takemoto, Y.1
  • 6
    • 52049088477 scopus 로고    scopus 로고
    • Using phosphoric acid
    • Using phosphoric acid: (c) Terada, M. Chem. Commun. 2008, 4097.
    • (2008) Chem. Commun. , pp. 4097
    • Terada, M.1
  • 7
    • 9644291545 scopus 로고    scopus 로고
    • For a review of the use of Brønsted acid catalysts for asymmetric protonation, see
    • For a review of the use of Brønsted acid catalysts for asymmetric protonation, see: Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3653
    • Duhamel, L.1    Duhamel, P.2    Plaquevent, J.-C.3
  • 8
    • 12344276522 scopus 로고    scopus 로고
    • For selected recent examples, see
    • For selected recent examples, see: (a) Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027.
    • (2004) Org. Lett. , vol.6 , pp. 5027
    • Huang, J.1    Corey, E.J.2
  • 17
    • 84886330800 scopus 로고    scopus 로고
    • For an example of stoichiometric usage of a chiral charged Brønsted acid for the reaction of a nonionic Lewis base, see
    • For an example of stoichiometric usage of a chiral charged Brønsted acid for the reaction of a nonionic Lewis base, see: (j) Jang, D. O.; Kim, S. Y. J. Am. Chem. Soc. 2008, 130, 16152.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 16152
    • Jang, D.O.1    Kim, S.Y.2
  • 24
    • 32244444791 scopus 로고    scopus 로고
    • For selected recent examples, see
    • For selected recent examples, see: (c) Terada, M.; Ube, H.; Yaguchi, Y. J. Am. Chem. Soc. 2006, 128, 1454.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1454
    • Terada, M.1    Ube, H.2    Yaguchi, Y.3
  • 39
    • 34547186015 scopus 로고    scopus 로고
    • For examples of achiral charged Brønsted acid catalyses, see
    • For examples of achiral charged Brønsted acid catalyses, see: (a) Takenaka, N.; Sarangthem, R. S.; Seerla, S. K. Org. Lett. 2007, 9, 2819.
    • (2007) Org. Lett. , vol.9 , pp. 2819
    • Takenaka, N.1    Sarangthem, R.S.2    Seerla, S.K.3
  • 41
    • 38349073963 scopus 로고    scopus 로고
    • For the nonenantioselective reaction, see: and references therein
    • For the nonenantioselective reaction, see: Ziyaei-Halimehjani, A.; Saidi, M. R. Tetrahedron Lett. 2008, 49, 1244, and references therein.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1244
    • Ziyaei-Halimehjani, A.1    Saidi, M.R.2
  • 48
    • 67650567501 scopus 로고    scopus 로고
    • a estimate for 2b•BArF
    • a estimate for 2b•BArF.
  • 49
    • 67650548093 scopus 로고    scopus 로고
    • When the reaction in entry 11 of Table 2 was performed in toluene at -15°C for 12 h, considerable loss of enantioselectivity was observed (96% yield, 72% ee)
    • When the reaction in entry 11 of Table 2 was performed in toluene at -15°C for 12 h, considerable loss of enantioselectivity was observed (96% yield, 72% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.