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Volumn 68, Issue 22, 2003, Pages 8505-8513

Ruthenium-Catalyzed Cyclopropanation of Alkenes Using Propargylic Carboxylates as Precursors of Vinylcarbenoids

Author keywords

[No Author keywords available]

Indexed keywords

INTERMOLECULAR CYCLOPROPANATION REACTIONS;

EID: 0142165973     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034841a     Document Type: Article
Times cited : (214)

References (65)
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    • Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1636
    • Trost, B.M.1    Tanoury, G.J.2
  • 14
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    • For the reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported: (a) Trost, B. M.; Hashmi, A. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1085
    • Trost, B.M.1    Hashmi, A.S.2
  • 28
    • 0037244612 scopus 로고    scopus 로고
    • and references therein
    • There are many reports on generation of carbene complexes such as the Dötz reaction via metathesis between alkynes and carbene complexes, For reviews on enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1 and references therein.
    • (2003) Synthesis , vol.1
    • Poulsen, C.S.1    Madsen, R.2
  • 32
    • 0000690866 scopus 로고    scopus 로고
    • Stoichiometric furan formations via the metathesis approach from similar compounds have been reported. See: (c) Jiang, D.; Herndon, J. W. Org. Lett. 2000, 2, 1267.
    • (2000) Org. Lett. , vol.2 , pp. 1267
    • Jiang, D.1    Herndon, J.W.2
  • 40
    • 0025338138 scopus 로고
    • Oxidative rearrangement of propargyl esters by palladium catalyst has been reported. See: (c) Kataoka, H.; Watanabe, K.; Goto, K. Tetrahedron Lett. 1990, 31, 4181.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4181
    • Kataoka, H.1    Watanabe, K.2    Goto, K.3
  • 44
    • 0142205675 scopus 로고    scopus 로고
    • note
    • 2-catalyzed case, cyclopropanation in DCE resulted in lower yield of 2a (74%) together with the formation of a substantial amount of allenyl acetate (23%).
  • 45
    • 0142205676 scopus 로고    scopus 로고
    • note
    • 3. Purification details are shown in the Experimental Section.
  • 46
    • 0142236581 scopus 로고    scopus 로고
    • note
    • The geometry of the alkenic part in the major product cis-2f was assigned to Z by X-ray diffraction analysis (see Supporting Information). Since the NMR data of trans-2f are similar to those of cis-2f with an exception of cyclopropane ring assignment, we assume that the geometry in trans-2f would be also Z.
  • 47
    • 0142174545 scopus 로고    scopus 로고
    • note
    • The reaction of If with styrene in DCE was not complete even after 36 h.
  • 50
    • 0142143715 scopus 로고    scopus 로고
    • note
    • Oxidative addition of propargylic acetate to a ruthenium complex leading to o-allenylruthenium acetate E followed by transposition of an acetate group from ruthenium to C-2 of the σ-allenyl ligand is another possible route to the vinylcarbenoid. However, experimental results of no formation of crossover products also rule out such a route where the acetoxy group might be liberated in the system.
  • 51
    • 33646142047 scopus 로고    scopus 로고
    • Generation of vinylcarbenoids from propargylic halides, acetates, and alcohols using transition metal hydride complexes has already been reported, and the complexes have been widely applied as metathesis catalysts. The mechanisms of these reactions, however, are apparently different from that of the present hydride-free case. (a) Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
    • (1997) Organometallics , vol.16 , pp. 3867
    • Wilhelm, T.E.1    Belderrain, T.R.2    Brown, S.N.3    Grubbs, R.H.4
  • 56
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    • note
    • 1H NMR spectrum of 2r or 2s, might support the configuration of transcyclopropane.
  • 57
    • 0009841005 scopus 로고    scopus 로고
    • The cascade reaction of carbenoid transfer cyclopropanation and [3, 3]sigmatropy has been developed by using a combination of diazoalkanes and rhodium- and copper-catalysts. For leading references of transition metal-catalyzed reactions, see: (a) Davies, H. M. L. Advance in Cycloaddit. 1999, 5, 119.
    • (1999) Advance in Cycloaddit , vol.5 , pp. 119
    • Davies, H.M.L.1
  • 64
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    • note
    • The syn stereochemistry of 2t was more clearly determined by NOE analysis. Thus, percentage increments (6% and 5%) in the area intensities of vinyl protons on a cyclopentene ring were observed by irradiation at the two methyl groups of an isopropylidene of 2t, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.