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Volumn 133, Issue 15, 2011, Pages 5656-5659

Direct catalytic asymmetric aminoallylation of aldehydes: Synergism of chiral and nonchiral Brønsted acids

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; ASYMMETRIC INDUCTION; CATALYST SYSTEM; HOMOALLYLIC AMINES; SYNERGISTIC INTERACTION;

EID: 79954512413     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1110865     Document Type: Article
Times cited : (70)

References (74)
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    • For studies on the catalyst structure, see
    • For studies on the catalyst structure, see: Hu, G.; Huang, L.; Huang, R. H.; Wulff, W. D. J. Am. Chem. Soc. 2009, 131, 15615-15617
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 15615-15617
    • Hu, G.1    Huang, L.2    Huang, R.H.3    Wulff, W.D.4
  • 58
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    • 2O as described in the Supporting Information and in ref 8i
    • 2O as described in the Supporting Information and in ref 8i.
  • 59
    • 79954519051 scopus 로고    scopus 로고
    • We are currently examining the structures of the catalysts from these ligands produced under the same conditions that give the boroxinates 9 for VANOL and VAPOL.
    • We are currently examining the structures of the catalysts from these ligands produced under the same conditions that give the boroxinates 9 for VANOL and VAPOL.
  • 64
    • 53249126965 scopus 로고    scopus 로고
    • For an example where a protic solvent can accelerate the rate of a reaction, see
    • For an example where a protic solvent can accelerate the rate of a reaction, see: Sickert, M.; Schneider, C. Angew. Chem., Int. Ed. 2008, 47, 3631-3634
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3631-3634
    • Sickert, M.1    Schneider, C.2
  • 65
    • 16844374787 scopus 로고    scopus 로고
    • For examples where intramolecular hydrogen bonding can enhance a Brønsted acid catalyst, see
    • For examples where intramolecular hydrogen bonding can enhance a Brønsted acid catalyst, see: Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924-1942
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1924-1942
    • Yamamoto, H.1    Futatsugi, K.2
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    • 79954488000 scopus 로고    scopus 로고
    • We thank Professor David MacMillan for suggesting the use of 5 Å molecular sieves.
    • We thank Professor David MacMillan for suggesting the use of 5 Å molecular sieves.
  • 67
    • 79954510356 scopus 로고    scopus 로고
    • The catalyst prepared from 2,4,6-trimethylphenol gives slightly higher inductions than the same catalyst prepared from phenol. For example, the catalyst from 2,4,6-trimethylphenol gives an 83% ee and 79% yield under the conditions in entry 15 of Table 1.
    • The catalyst prepared from 2,4,6-trimethylphenol gives slightly higher inductions than the same catalyst prepared from phenol. For example, the catalyst from 2,4,6-trimethylphenol gives an 83% ee and 79% yield under the conditions in entry 15 of Table 1.
  • 68
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    • It has been shown that boroxinate formation can be induced by amines:, Ph. D. Thesis, Michigan State University.
    • It has been shown that boroxinate formation can be induced by amines: Hu, G., Ph. D. Thesis, Michigan State University, 2007.
    • (2007)
    • Hu, G.1
  • 69
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    • For the synthesis of coniine using ring-closing metathesis, see
    • For the synthesis of coniine using ring-closing metathesis, see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269-2276
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2269-2276
    • Kumareswaran, R.1    Hassner, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.