메뉴 건너뛰기




Volumn 2, Issue 4, 2004, Pages 446-448

Phosphine oxides as efficient neutral coordinate-organocatalysts for stereoselective allylation of N-acylhydrazones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBON; HYDROGEN PEROXIDE; KETONES; OXIDATION; PHOSPHORUS COMPOUNDS; SILANES; SOLUBILITY; STEREOCHEMISTRY;

EID: 1342344956     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b315037b     Document Type: Article
Times cited : (44)

References (25)
  • 2
    • 0001503042 scopus 로고    scopus 로고
    • S. Kobayashi and K. Nishio, J. Org. Chem., 1994, 59, 6620; K. Iseki, S. Mizuno, Y. Kuroki and Y. Kobayashi, Tetrahedron, 1999, 55, 997.
    • (1994) J. Org. Chem. , vol.59 , pp. 6620
    • Kobayashi, S.1    Nishio, K.2
  • 6
  • 10
    • 0037871675 scopus 로고    scopus 로고
    • S. Kobayashi, C. Ogawa, H. Konishi and M. Sugiura, J. Am. Chem. Soc., 2003, 125, 6610; A. Massa, A. V. Malcov, P. Kocovsky and A. Scettri, Tetrahedron Lett., 2003, 44, 7179; G. J. Rowlands and W. K. Barnes, Chem. Commun., 2003, 2712.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6610
    • Kobayashi, S.1    Ogawa, C.2    Konishi, H.3    Sugiura, M.4
  • 11
    • 0041508449 scopus 로고    scopus 로고
    • S. Kobayashi, C. Ogawa, H. Konishi and M. Sugiura, J. Am. Chem. Soc., 2003, 125, 6610; A. Massa, A. V. Malcov, P. Kocovsky and A. Scettri, Tetrahedron Lett., 2003, 44, 7179; G. J. Rowlands and W. K. Barnes, Chem. Commun., 2003, 2712.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 7179
    • Massa, A.1    Malcov, A.V.2    Kocovsky, P.3    Scettri, A.4
  • 12
    • 0242609866 scopus 로고    scopus 로고
    • S. Kobayashi, C. Ogawa, H. Konishi and M. Sugiura, J. Am. Chem. Soc., 2003, 125, 6610; A. Massa, A. V. Malcov, P. Kocovsky and A. Scettri, Tetrahedron Lett., 2003, 44, 7179; G. J. Rowlands and W. K. Barnes, Chem. Commun., 2003, 2712.
    • (2003) Chem. Commun. , pp. 2712
    • Rowlands, G.J.1    Barnes, W.K.2
  • 14
  • 15
  • 18
    • 0034614084 scopus 로고    scopus 로고
    • S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2000, 122, 12021; S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2001, 123, 9488.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12021
    • Denmark, S.E.1    Fu, J.2
  • 19
    • 0035955158 scopus 로고    scopus 로고
    • S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2000, 122, 12021; S. E. Denmark and J. Fu, J. Am. Chem. Soc., 2001, 123, 9488.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9488
    • Denmark, S.E.1    Fu, J.2
  • 20
    • 1342318484 scopus 로고    scopus 로고
    • note
    • We also tested these reactions using three equivalents of DMSO. In the case of the aromatic substrate, the desired products were hardly obtained; Z-crotylation 9% (synlanti = 3/97), E-crotylation 3% (synlanti = not determined). As for the α,β-unsaturated substrate, even allylation did not proceed using DMSO.
  • 22
    • 0035966240 scopus 로고    scopus 로고
    • Triphenylphosphine polystyrene (Novabiochem®, polymer matrix: copoly(styrene-1% DVB), 100-200 mesh) was oxidized according to the reported procedure: T. Shimada, H. Kurushima, Y.-H. Cho and T. Hayashi, J. Org. Chem., 2001, 66, 8854.
    • (2001) J. Org. Chem. , vol.66 , pp. 8854
    • Shimada, T.1    Kurushima, H.2    Cho, Y.-H.3    Hayashi, T.4
  • 24
    • 1342318485 scopus 로고    scopus 로고
    • note
    • The elemental analysis showed that PS-phosphine oxide 2 contained 4.2% phosphorous atoms.
  • 25
    • 1342318486 scopus 로고    scopus 로고
    • note
    • PS-phosphine oxide 2 is not soluble but swollen in dichloromethane. After the reaction, 2 was recovered quantitatively by simple filtration and washing (water, methanol, diethyl ether, tetrahydrofuran, and dichloromethane). It might be possible that one or two phosphine oxide components in 2 activate allyltrichlorosilane in the transition state, though the latter might be less prominent in the polymer matrix.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.