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Volumn 60, Issue 6, 2004, Pages 1375-1383

Pentadienyl transfer reagents based on zirconium: Preparation and reactions with carbonyl compounds

Author keywords

Homoallylic alcohols; Pentadienylation reaction; Stereocontrol; Zirconium

Indexed keywords

ALCOHOL; ALLYL COMPOUND; CARBONYL DERIVATIVE; ETHER DERIVATIVE; REAGENT; ZIRCONIUM; ZIRCONOCENE;

EID: 1642431611     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.065     Document Type: Article
Times cited : (14)

References (40)
  • 2
    • 0002446724 scopus 로고
    • B.M. Trost, I. Fleming, Heathcock C.W. Oxford: Pergamon
    • Roush W. Trost B.M., Fleming I., Heathcock C.W. Comprehensive Organic Synthesis. Vol. 2:1991;1 Pergamon, Oxford.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.1
  • 3
    • 0001823413 scopus 로고
    • Leading references for pentadienylmetals: Li: (a)
    • Leading references for pentadienylmetals: Li: (a) Gérard F., Miginiac P. Bull. Soc. Chim. Fr. 1974;1924.
    • (1974) Bull. Soc. Chim. Fr. , pp. 1924
    • Gérard, F.1    Miginiac, P.2
  • 19
    • 85030890548 scopus 로고    scopus 로고
    • The use of alcohol derivatives, i.e. acetates or carbonates, for preparing pentadienylmetals is limited to titanium and chromium complexes, see Refs. 2i,k
    • The use of alcohol derivatives, i.e. acetates or carbonates, for preparing pentadienylmetals is limited to titanium and chromium complexes, see Refs. 2i,k.
  • 28
    • 85030898179 scopus 로고    scopus 로고
    • The pentadienyl ethers are stable compounds in comparison with pentadienyl bromides
    • The pentadienyl ethers are stable compounds in comparison with pentadienyl bromides.
  • 29
    • 85030894197 scopus 로고    scopus 로고
    • For the 1,3-metallotropic rearrangement with Zr, see: (a) Ref. 5
    • For the 1,3-metallotropic rearrangement with Zr, see: (a) Ref. 5.
  • 30
    • 0030607168 scopus 로고    scopus 로고
    • and references therein
    • Wipf P., Jahn H. Tetrahedron. 52:1996;12853. and references therein.
    • (1996) Tetrahedron , vol.52 , pp. 12853
    • Wipf, P.1    Jahn, H.2
  • 31
    • 85030904222 scopus 로고    scopus 로고
    • We have noticed that this procedure is also useful for the preparation of allylzirconocenes from allylic ethers
    • We have noticed that this procedure is also useful for the preparation of allylzirconocenes from allylic ethers.
  • 32
    • 85030897535 scopus 로고    scopus 로고
    • The anti configuration was defined with reference to the simpler allylmetalation reactions, by considering pentadienylzirconiums as alkenyl-substituted allylmetals. The anti configuration was undoubtedly assigned to the major isomers by a cyclization method. For an example see Ref. 4
    • The anti configuration was defined with reference to the simpler allylmetalation reactions, by considering pentadienylzirconiums as alkenyl-substituted allylmetals. The anti configuration was undoubtedly assigned to the major isomers by a cyclization method. For an example see Ref. 4.
  • 36
    • 85030892448 scopus 로고    scopus 로고
    • 3 in THF was added to the reaction mixture
    • 3 in THF was added to the reaction mixture.
  • 37
    • 85030914315 scopus 로고    scopus 로고
    • The predominant syn diastereoselection in the Lewis acid-mediated allylic tin-aldehyde condensation reactions was rationalized similarly, see Ref. 1
    • The predominant syn diastereoselection in the Lewis acid-mediated allylic tin-aldehyde condensation reactions was rationalized similarly, see Ref. 1.
  • 38
    • 85030913863 scopus 로고    scopus 로고
    • note
    • The formation of the ε-regioisomeric by-product 8 from the ether 6c in the presence of a Lewis acid (see Table 3) also corroborates a non-cyclic mechanism.
  • 39
    • 67650317827 scopus 로고
    • For example, different open transition structures have been considered for the Lewis acid-mediated allylmetalation reactions, see: (a)
    • For example, different open transition structures have been considered for the Lewis acid-mediated allylmetalation reactions, see: (a) Denmark S.E., Weber E.J. Helv. Chim. Acta. 66:1983;1655.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 1655
    • Denmark, S.E.1    Weber, E.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.