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Volumn 66, Issue 34, 2010, Pages 7012-7016

Domino reactions starting from alkynyl esters tethered to 2-methyl-1,3-cycloalkanediones. Efficient access to polyfunctionalized diquinanes, allenoates, and oxetanes

Author keywords

Allenoate; Diquinane; Domino reactions; Molecular sieves; Oxetane; TBAF

Indexed keywords

2 METHYL 1,3 CYCLOALKANEDIONE DERIVATIVE; ALLENE DERIVATIVE; ALLENOATE DERIVATIVE; CYCLOALKANE DERIVATIVE; DIQUINANE DERIVATIVE; OXETANE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; QUININE DERIVATIVE; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

EID: 77955466358     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.025     Document Type: Article
Times cited : (7)

References (36)
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    • note
    • The Hajos-Parrish-Eder-Sauer-Wiechert reaction is one of the most representative example leading to 5-6 and 6-6 fused rings:
  • 2
    • 77955468743 scopus 로고
    • German Patent DE 2,102,623
    • Hajos, Z.G.; Parrish, D.R. German Patent DE 2,102,623, 1971.
    • (1971)
    • Hajos, Z.G.1    Parrish, D.R.2
  • 7
    • 33947667037 scopus 로고    scopus 로고
    • For reviews dealing with the synthesis and reactivity of allenes
    • For reviews dealing with the synthesis and reactivity of allenes, see: K.M. Brummond, and J.E. DeForrest Synthesis 2007 795 818
    • (2007) Synthesis , pp. 795-818
    • Brummond, K.M.1    Deforrest, J.E.2
  • 9
    • 4544320494 scopus 로고    scopus 로고
    • N. Krause, A.S.K. Hashmi, Wiley-VCH Weinheim
    • N. Krause, A.S.K. Hashmi, Modern allene chemistry Vol. 1 and 2 2004 Wiley-VCH Weinheim
    • (2004) Modern Allene Chemistry , vol.12
  • 10
    • 60949108432 scopus 로고    scopus 로고
    • For relevant references concerning the reactivity of allenoates
    • For relevant references concerning the reactivity of allenoates, see: L.-P. Liu, B. Xu, and G.B. Hammond Org. Lett. 10 2008 3887 3890
    • (2008) Org. Lett. , vol.10 , pp. 3887-3890
    • Liu, L.-P.1    Xu, B.2    Hammond, G.B.3
  • 15
    • 67650323881 scopus 로고    scopus 로고
    • For oxetanes see
    • For oxetanes see: Y. Ye, C. Zheng, and R. Fan Org. Lett. 11 2009 3156 3159
    • (2009) Org. Lett. , vol.11 , pp. 3156-3159
    • Ye, Y.1    Zheng, C.2    Fan, R.3
  • 20
    • 0030458427 scopus 로고    scopus 로고
    • For the reactivity of 2-methyl-1,3-cycloalkanediones tethered to electron-deficient functional groups
    • For the reactivity of 2-methyl-1,3-cycloalkanediones tethered to electron-deficient functional groups, see: D. Schinzer, T. Blume, and P.G. Jones Angew. Chem., Int. Ed. Engl. 35 1996 2500 20502
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2500-20502
    • Schinzer, D.1    Blume, T.2    Jones, P.G.3
  • 25
    • 77955471011 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra. Allenoate 11 was isolated as a mixture of two isomers bearing a cis ring junction (yield: 21%; ratio: 1/1.3) along with 1 isomer bearing a trans ring junction (34%).
  • 26
    • 77955472485 scopus 로고    scopus 로고
    • Allenoate 11 bearing a trans ring junction and E allenoate was obtained by column chromatography of the crude mixture of allenoate. CCDC-705046 contains the supplementary crystallographic data for compound 11. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif. CCDC-637164 contains the supplementary crystallographic data for compound 10. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif.
  • 27
    • 0344965589 scopus 로고
    • For oxetanes bearing an electrophilic exocyclic double bond
    • For oxetanes bearing an electrophilic exocyclic double bond see: G. Ahlgren J. Org. Chem. 38 1973 1369-1374
    • (1973) J. Org. Chem. , vol.38
    • Ahlgren, G.1
  • 32
    • 77955471098 scopus 로고    scopus 로고
    • note
    • The synthesis of the acetate derivative derived from acetylenic ω-ketoester 7 was also carried out but led to a complex mixture of inseparable isomers; therefore, the reactivity of the latter toward TBAF was not studied. On the other hand, the formation of the syn acetate derived from the acetylenic ω-ketoester 4 took place in less than 10% yield so that it's reactivity toward TBAF was also not studied.
  • 33
    • 77955469389 scopus 로고    scopus 로고
    • note
    • The 4 molecular sieves were activated by heating at 250°C/0.01 mm Hg for 12 h and then stored at room temperature under argon.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.