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Volumn 51, Issue 47, 2010, Pages 6093-6097

Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans

Author keywords

Adjacent bis tetrahydrofurans; Alkylation reaction; Michael reaction; Tandem reactions; Tetrahydrofuran

Indexed keywords

CARBONIC ACID; ETHER; FURAN DERIVATIVE; IODIDE;

EID: 77958455434     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.008     Document Type: Article
Times cited : (25)

References (51)
  • 1
    • 15844366864 scopus 로고
    • For reviews on tetrahydrofuran synthesis, see: T.L.B. Boivin Tetrahedron 43 1987 3309
    • (1987) Tetrahedron , vol.43 , pp. 3309
    • Boivin, T.L.B.1
  • 20
    • 0028845178 scopus 로고
    • For some selected examples of Stetter reaction in the synthesis THF and THPs, see: E. Ciganek Synthesis 1995 1311
    • (1995) Synthesis , pp. 1311
    • Ciganek, E.1
  • 31
    • 33751390926 scopus 로고
    • For some selected examples of tandem alkylation-Michael reaction sequence for the synthesis of heterocycles and carbacycles, see: R.A. Bunce, C.J. Peeples, and P.B. Jones J. Org. Chem. 57 1992 1727
    • (1992) J. Org. Chem. , vol.57 , pp. 1727
    • Bunce, R.A.1    Peeples, C.J.2    Jones, P.B.3
  • 41
    • 77958503318 scopus 로고    scopus 로고
    • note
    • 3) δ 4.42 (td, J = 8.4, 5.2 Hz, 1H), 4.40-4.15 (m, 5H), 3.30 (AB, J = 16.0 Hz, 1H), 3.08 (AB, J = 16.0 Hz, 1H), 3.00-2.80 (m, 2H), 1.33 (t, J = 7.2 Hz, 3H), 1.27 (t, J = 7.2 Hz, 3H);
  • 42
    • 77958490224 scopus 로고    scopus 로고
    • note
    • 4). Evaporation of the solvent and purification of the reisdue on a silica gel column using ethyl acetate/hexanes (1:12) as eluent furnished the THF derivative 1aa (61 mg, 79%) as a colourless oil.
  • 45
    • 77958454298 scopus 로고    scopus 로고
    • note
    • 7 unit cell parameters: a 10.6929(12) b 8.5506(10) c 11.5532(15) β 107.922(5) space group P21 CCDC No. 787426. CCDC Nos. 787425 and 787426 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.