메뉴 건너뛰기




Volumn , Issue 18, 2012, Pages 3377-3384

C-C coupling of acyclic nitronates with silyl ketene acetals under silyl triflate catalysis: Reactivity umpolung of aliphatic nitro compounds

Author keywords

Amino acids; C C coupling; Hydrogenation; Nitro compounds; Umpolung

Indexed keywords


EID: 84862200982     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200239     Document Type: Article
Times cited : (22)

References (39)
  • 2
    • 0018454939 scopus 로고
    • Angew. Chem. Int. Ed. Engl. 1979, 18, 239 - 258.
    • D. Seebach, Angew. Chem. 1979, 91, 259; Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258.
    • (1979) Angew. Chem. , vol.91 , pp. 259
    • Seebach, D.1
  • 3
    • 0346339657 scopus 로고    scopus 로고
    • For a recent review on the Nef reaction, see:, R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047.
    • (2004) Tetrahedron , vol.60 , pp. 1017-1047
    • Ballini, R.1    Petrini, M.2
  • 5
    • 0001165505 scopus 로고
    • Org. React. 1990, 38, 655 -792.
    • It is noteworthy that the Nef reaction as a tool for reactivity inversion initially was considered with acyl synthon umpolung through alkylation of AN followed by the Nef reaction. This consideration reveals AN as equivalents of the acyl anion synthon; see, for example, the review:, H. W. Pinnick, Org. React. 1990, 38, 655-792. To the best of our knowledge, the Nef reaction as a route for umpolung of AN themselves was considered for the first time in the paper:, H. W. Pinnick, Org. React. 1990, 38, 655 -792.
    • (1990) Org. React. , vol.38 , pp. 655-792
    • Pinnick, H.W.1    Pinnick, H.W.2
  • 8
    • 0004370801 scopus 로고
    • [5b,8,9]) were realized in non-basic solvents (such as dichloromethane or trifluoroacetic acid) or without solvent at all, and under these conditions acid catalysis for 1 to 2 tautomerization is plausible. Furthermore, aci-nitro forms may be generated from isolated nitronate salts by the action of acid, as kinetic protonation of anion A takes place at the oxygen atom.
    • (1971) Can. J. Chem. , vol.49 , pp. 3493-3501
    • Edward, J.T.1    Tremaine, P.H.2
  • 9
    • 6344277038 scopus 로고    scopus 로고
    • For the estimation of the nucleophilicity of anions A see:, T. Bug, T. Lemek, H. Mayr, J. Org. Chem. 2004, 69, 7565-7576.
    • (2004) J. Org. Chem. , vol.69 , pp. 7565-7576
    • Bug, T.1    Lemek, T.2    Mayr, H.3
  • 27
    • 84862182325 scopus 로고    scopus 로고
    • Yu. A. Khomutova, A. A. Mikhaylov, S. L. Ioffe, unpublished data
    • Yu. A. Khomutova, A. A. Mikhaylov, S. L. Ioffe, unpublished data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.