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Volumn 64, Issue 5, 2008, Pages 915-925

A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates

Author keywords

(Trialkylsilyl)vinylketenes; Benzannulation; Electrocyclic ring closure; Ynolates

Indexed keywords

AROMATIC COMPOUND; BENZOFURAN DERIVATIVE; BENZOQUINONE DERIVATIVE; BENZOXEPIN DERIVATIVE; BENZOXOCINE; HETEROAROMATIC COMPOUND; KETENE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM YNOLATE; OXOCIN DERIVATIVE; PHENOL DERIVATIVE; RESORCINOL DERIVATIVE; RESORCINOL MONOSILYL ETHER; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 37149023304     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.113     Document Type: Article
Times cited : (33)

References (67)
  • 2
    • 37149026711 scopus 로고    scopus 로고
    • Reviewed in:
  • 4
    • 33748535256 scopus 로고    scopus 로고
    • John Wiley and Sons, Hoboken, NJ
    • Tidwell T.T. Ketenes. 2nd ed. (2006), John Wiley and Sons, Hoboken, NJ
    • (2006) Ketenes. 2nd ed.
    • Tidwell, T.T.1
  • 9
    • 0034687190 scopus 로고    scopus 로고
    • For applications in the total synthesis of natural products, see: and references cited therein
    • For applications in the total synthesis of natural products, see:. Dudley G.B., Takaki K.S., Cha D.D., and Danheiser R.L. Org. Lett. 2 (2000) 3407 and references cited therein
    • (2000) Org. Lett. , vol.2 , pp. 3407
    • Dudley, G.B.1    Takaki, K.S.2    Cha, D.D.3    Danheiser, R.L.4
  • 10
    • 37149031908 scopus 로고    scopus 로고
    • For reviews of the chemistry of silylketenes, see:
  • 11
    • 37149045652 scopus 로고    scopus 로고
    • Danheiser R.L. (Ed), Thieme, Stuttgart, Germany
    • George D.M., and Danheiser R.L. In: Danheiser R.L. (Ed). Science of Synthesis Vol. 23 (2006), Thieme, Stuttgart, Germany 53-99
    • (2006) Science of Synthesis , vol.23 , pp. 53-99
    • George, D.M.1    Danheiser, R.L.2
  • 12
    • 0012749364 scopus 로고    scopus 로고
    • Fleming I. (Ed), Thieme, Stuttgart, Germany
    • Pons J.-M., and Kocienski P.J. In: Fleming I. (Ed). Science of Synthesis Vol. 4 (2001), Thieme, Stuttgart, Germany 657-668
    • (2001) Science of Synthesis , vol.4 , pp. 657-668
    • Pons, J.-M.1    Kocienski, P.J.2
  • 21
    • 37149021385 scopus 로고    scopus 로고
    • For related reactions involving silylated bisketenes, see:
  • 29
    • 37149038283 scopus 로고    scopus 로고
    • For reviews of the chemistry of ynolates, see:
  • 37
    • 0011847933 scopus 로고
    • For a discussion of the 6π electrocyclization of 3-oxido-1,3,5-hexatrienes, see:
    • For a discussion of the 6π electrocyclization of 3-oxido-1,3,5-hexatrienes, see:. Magnus P. Nouv. J. Chim. 2 (1978) 555
    • (1978) Nouv. J. Chim. , vol.2 , pp. 555
    • Magnus, P.1
  • 38
    • 37149017425 scopus 로고    scopus 로고
    • For prior examples of 6π electrocyclization reactions involving enolate derivatives, see:
  • 43
    • 0033595558 scopus 로고    scopus 로고
    • For a recent theoretical study and leading references, see:
    • For a recent theoretical study and leading references, see:. Takahashi M., and Kira M. J. Am. Chem. Soc. 121 (1999) 8597
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8597
    • Takahashi, M.1    Kira, M.2
  • 49
    • 84991182227 scopus 로고
    • The metalation of 1-phenyl-4-penten-1-yne with MeLi has previously been reported:
    • The metalation of 1-phenyl-4-penten-1-yne with MeLi has previously been reported:. Klein J., Brenner S., and Medlik A. Isr. J. Chem. 9 (1971) 177
    • (1971) Isr. J. Chem. , vol.9 , pp. 177
    • Klein, J.1    Brenner, S.2    Medlik, A.3
  • 50
    • 37149000664 scopus 로고    scopus 로고
    • note
    • Separation of these phenols from byproducts was not possible without significant losses, precluding an accurate determination of yield.
  • 51
    • 33644763028 scopus 로고    scopus 로고
    • A related thermal 1,3 carbon to oxygen shift in a 2-tert-butyldimethylsilyl-substituted phenol has recently been reported:
    • A related thermal 1,3 carbon to oxygen shift in a 2-tert-butyldimethylsilyl-substituted phenol has recently been reported:. Eastham S.A., Ingham S.P., Hallett M.R., Herbert J., Quayle P., and Raftery J. Tetrahedron Lett. 47 (2006) 2299
    • (2006) Tetrahedron Lett. , vol.47 , pp. 2299
    • Eastham, S.A.1    Ingham, S.P.2    Hallett, M.R.3    Herbert, J.4    Quayle, P.5    Raftery, J.6
  • 52
    • 2742593404 scopus 로고
    • Thermal 1,3-rearrangement of 2-trimethylsilylphenol has previously been described:
    • Thermal 1,3-rearrangement of 2-trimethylsilylphenol has previously been described:. Cooper G.D. J. Am. Chem. Soc. 26 (1961) 925
    • (1961) J. Am. Chem. Soc. , vol.26 , pp. 925
    • Cooper, G.D.1
  • 53
    • 2942609168 scopus 로고    scopus 로고
    • For a review of palladium-catalyzed cyclizations of this type, see:
    • For a review of palladium-catalyzed cyclizations of this type, see:. Zeni G., and Larock R.C. Chem. Rev. 104 (2004) 2285
    • (2004) Chem. Rev. , vol.104 , pp. 2285
    • Zeni, G.1    Larock, R.C.2
  • 54
    • 33947093389 scopus 로고
    • These conditions have been employed by Hegedus for the cyclization of 2-allylanilines to indoles, see:
    • These conditions have been employed by Hegedus for the cyclization of 2-allylanilines to indoles, see:. Hegedus L.S., Allen G.F., Bozell J.J., and Waterman E.L. J. Am. Chem. Soc. 100 (1978) 5800
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5800
    • Hegedus, L.S.1    Allen, G.F.2    Bozell, J.J.3    Waterman, E.L.4
  • 56
    • 37149004944 scopus 로고    scopus 로고
    • For reviews of the application of ring closing metathesis to the preparation of heterocycles, see:
  • 66
    • 37149039844 scopus 로고    scopus 로고
    • note
    • LiHMDS solution was prepared by the reaction of HMDS (2.8 mL, 2.1 g, 13 mmol) with 5.0 mL of BuLi solution (2.49 M in hexanes, 13 mmol) in 6.4 mL of THF.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.