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Volumn 1, Issue 6, 2014, Pages 614-624

NHC-catalyzed homoenolate reaction of enals and nitroalkenes: Computational study of mechanism, chemoselectivity and stereoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DISSOCIATION; HYDROGEN BONDS; ORGANIC COMPOUNDS; PROTON TRANSFER; STEREOSELECTIVITY;

EID: 84936880295     PISSN: 20524110     EISSN: 20524129     Source Type: Journal    
DOI: 10.1039/c4qo00036f     Document Type: Article
Times cited : (32)

References (86)
  • 11
    • 0001070365 scopus 로고
    • ied. L. A. Paquette, Wiley, New York
    • H. Stetter and H. Kuhlmann, in Org. React., ed., L. A. Paquette, Wiley, New York, 1991, vol. 40, pp. 407-496
    • (1991) Org. React. , vol.40 , pp. 407-496
    • Stetter, H.1    Kuhlmann, H.2
  • 71
    • 43049141516 scopus 로고    scopus 로고
    • The M06 method has been used in many metal free systems for single-point energy calculations
    • Y. Zhao D. G. Truhlar Theor. Chem. Acc. 2008 120 215
    • (2008) Theor. Chem. Acc. , vol.120 , pp. 215
    • Zhao, Y.1    Truhlar, D.G.2
  • 79
    • 0035958483 scopus 로고    scopus 로고
    • We took the proton transfer step (Path-f) as an example to investigate the influence of hydrogen bonding, and it turned out that hydrogen bonding induced by solvent is unlikely to occur. Please see ESI for details Mechanism Path-g was also examined in which C1-H bond of Int1 break first via TS-g. See the ESI for more details We have investigated the formation of the diastereomer of Int1 and the transition states for conversion of both diastereomers into Int2 and Int5. Detailed results are given in the ESI. Other three attack mode (1-Si, 4-Si), (1-Re, 4-Re), (1-Re, 4-Si) of Int5, and another three attack mode (1-Si, 4-Si), (1-Re, 4-Re), (1-Si, 4-Re) of Int2 in Stetter reaction are placed in ESI.
    • M. J. White F. J. Leeper J. Org. Chem. 2001 66 5124
    • (2001) J. Org. Chem. , vol.66 , pp. 5124
    • White, M.J.1    Leeper, F.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.