메뉴 건너뛰기




Volumn 60, Issue 44, 2004, Pages 9795-9833

When the Pauson-Khand and Pauson-Khand type reactions go awry: A plethora of unexpected results

Author keywords

Alkyne; Cycloaddition; Cyclopentenones; Pauson Khand reaction

Indexed keywords

ALKADIENE; ALKENE; ALKYNE; CARBENE; CYCLOPENTENONE DERIVATIVE; KETONE DERIVATIVE; ORGANOMETALLIC COMPOUND;

EID: 4644324093     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.072     Document Type: Review
Times cited : (181)

References (276)
  • 5
    • 0001334715 scopus 로고
    • B.M. Trost, Fleming I. Oxford: Pergamon
    • Schore N.E. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 5:1991;1037 Pergamon, Oxford
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 6
    • 0001136410 scopus 로고
    • E.W. Abel, F.A. Stone, Wilkinson G. New York: Elsevier
    • Schore N.E. Abel E.W., Stone F.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 12:1995;703 Elsevier, New York
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 703
    • Schore, N.E.1
  • 13
    • 0038665161 scopus 로고    scopus 로고
    • For a recent review on the catalytic PKR, see:
    • For a recent review on the catalytic PKR, see: Gibson S.E., Stevenazzi A. Angew. Chem., Int. Ed. 42:2003;1800
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1800
    • Gibson, S.E.1    Stevenazzi, A.2
  • 17
    • 37049132156 scopus 로고
    • While the identity of the Pauson-Khand cycloadduct was first reported in 1973 (Ref. 14), the formation of 'ketonic products' from the reaction of dicobalthexacarbonyl-complexed alkynes with norbornadiene and acetylene was first reported in 1971 by Pauson and co-workers
    • While the identity of the Pauson-Khand cycloadduct was first reported in 1973 (Ref. 14), the formation of 'ketonic products' from the reaction of dicobalthexacarbonyl-complexed alkynes with norbornadiene and acetylene was first reported in 1971 by Pauson and co-workers Khand I.U., Knox G.R., Pauson P.L., Watts W.E. J. Chem. Soc., Chem. Commun. 1971;36
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 36
    • Khand, I.U.1    Knox, G.R.2    Pauson, P.L.3    Watts, W.E.4
  • 43
    • 4644236638 scopus 로고    scopus 로고
    • For an excellent compilation of dienes formed as by-products in the PKR prior to 1990, see Ref. 4
    • For an excellent compilation of dienes formed as by-products in the PKR prior to 1990, see Ref. 4
  • 63
    • 0037692311 scopus 로고    scopus 로고
    • For a general reference on the mechanism of transition metal-catalyzed diene formation, see:
    • For a general reference on the mechanism of transition metal-catalyzed diene formation, see: Lloyd-Jones G.C. Org. Biomol. Chem. 1:2003;215
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 215
    • Lloyd-Jones, G.C.1
  • 96
    • 0038221244 scopus 로고
    • Reactions of 1,6-enynes with metal carbenes yield vinyl cyclopropanes. See for example:
    • Reactions of 1,6-enynes with metal carbenes yield vinyl cyclopropanes. See for example: Hoye T.R., Rehberg G.M. Organometallics. 8:1989;2070
    • (1989) Organometallics , vol.8 , pp. 2070
    • Hoye, T.R.1    Rehberg, G.M.2
  • 108
    • 0037149440 scopus 로고    scopus 로고
    • Methylidynetricobalt nonacarbonyl has been used to catalyze the cyclotrimerization of alkynes that were originally seen as unanticipated by-products in the Pauson-Khand reaction
    • Methylidynetricobalt nonacarbonyl has been used to catalyze the cyclotrimerization of alkynes that were originally seen as unanticipated by-products in the Pauson-Khand reaction Sugihara T., Wakabayashi A., Nagai Y., Takao H., Imagawa H., Nishizawa M. Chem. Commun. 2002;576
    • (2002) Chem. Commun. , pp. 576
    • Sugihara, T.1    Wakabayashi, A.2    Nagai, Y.3    Takao, H.4    Imagawa, H.5    Nishizawa, M.6
  • 113
    • 84985611234 scopus 로고
    • A clever tandem vinylcyclopropane-cyclopentene rearrangement via a Pauson-Khand reaction was reported by de Meijere; see:
    • A clever tandem vinylcyclopropane-cyclopentene rearrangement via a Pauson-Khand reaction was reported by de Meijere; see: Keyaniyan S., Apel M., Richmond J.P., de Meijere A. Angew. Chem., Int. Ed. Engl. 24:1985;770
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 770
    • Keyaniyan, S.1    Apel, M.2    Richmond, J.P.3    De Meijere, A.4
  • 150
    • 4644228638 scopus 로고    scopus 로고
    • PhD Dissertation, West Virginia University
    • Kerekes, A. D. PhD Dissertation, West Virginia University, 2001.
    • (2001)
    • Kerekes, A.D.1
  • 151
    • 0035808912 scopus 로고    scopus 로고
    • A cobalt containing by-product was recently isolated from reactions of phosphine-substituted cobalt carbonyl complexes
    • A cobalt containing by-product was recently isolated from reactions of phosphine-substituted cobalt carbonyl complexes Comely A.C., Gibson S.E., Stevanazzi A., Hales N.J. Tetrahedron Lett. 42:2001;1183
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1183
    • Comely, A.C.1    Gibson, S.E.2    Stevanazzi, A.3    Hales, N.J.4
  • 181
    • 4644226906 scopus 로고    scopus 로고
    • Use of a 1,2-isopropylidenedioxyfuranoside scaffold led to high endo selectivity in the PK reaction generating pyran derivatives. Ref. 158
    • Use of a 1,2-isopropylidenedioxyfuranoside scaffold led to high endo selectivity in the PK reaction generating pyran derivatives. Ref. 158
  • 261
    • 0034840336 scopus 로고    scopus 로고
    • For PK reactions of fluorine-containing enynes, see:
    • For PK reactions of fluorine-containing enynes, see: Ishizaki M., Suzuki D., Hoshimo O. J. Fluorine Chem. 111:2001;81
    • (2001) J. Fluorine Chem. , vol.111 , pp. 81
    • Ishizaki, M.1    Suzuki, D.2    Hoshimo, O.3
  • 273
    • 0034638410 scopus 로고    scopus 로고
    • 2/(S)-BINAP catalyzed intermolecular cycloaddition of norbornene with 1-phenylpropyne gave a 10:1 mixture of regioisomers, with the major product having the phenyl group adjacent to the carbonyl
    • 2/(S)-BINAP catalyzed intermolecular cycloaddition of norbornene with 1-phenylpropyne gave a 10:1 mixture of regioisomers, with the major product having the phenyl group adjacent to the carbonyl Shibata T., Takagi K. J. Am. Chem. Soc. 122:2000;9852
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9852
    • Shibata, T.1    Takagi, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.