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Volumn 45, Issue 13, 2004, Pages 2805-2808

Ring-closing metathesis toward the synthesis of 2,5-dihydrofuran and 2,5-dihydropyrrole skeletons from Baylis-Hillman adducts

Author keywords

2,5 Dihydrofuran; 2,5 Dihydropyrrole; Baylis Hillman adducts; Ring closing metathesis

Indexed keywords

2,5 DIHYDROPYRROLE; DIHYDROFURAN; FURAN DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1542358701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.047     Document Type: Article
Times cited : (62)

References (34)
  • 5
    • 0041657593 scopus 로고    scopus 로고
    • 3 many research groups reported on the reactions involving the disubstituted electron-deficient alkenes, see:
    • 3 many research groups reported on the reactions involving the disubstituted electron-deficient alkenes, see: Hekking K.F.W., van Delft F.L., Rutjes F.P.J.T. Tetrahedron. 59:2003;6751.
    • (2003) Tetrahedron , vol.59 , pp. 6751
    • Hekking, K.F.W.1    Van Delft, F.L.2    Rutjes, F.P.J.T.3
  • 15
    • 0042530225 scopus 로고    scopus 로고
    • Our recent publications on the Baylis-Hillman chemistry:
    • Our recent publications on the Baylis-Hillman chemistry: Lee K.Y., Kim J.M., Kim J.N. Tetrahedron Lett. 44:2003;6737.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6737
    • Lee, K.Y.1    Kim, J.M.2    Kim, J.N.3
  • 20
    • 0037434036 scopus 로고    scopus 로고
    • and further references cited therein
    • Lee K.Y., Kim J.M., Kim J.N. Tetrahedron. 59:2003;385. and further references cited therein.
    • (2003) Tetrahedron , vol.59 , pp. 385
    • Lee, K.Y.1    Kim, J.M.2    Kim, J.N.3
  • 21
    • 0000182934 scopus 로고    scopus 로고
    • For the synthesis of 2,5-dihydropyrrole derivatives, see:
    • For the synthesis of 2,5-dihydropyrrole derivatives, see: Xu Z., Lu X. J. Org. Chem. 63:1998;5031.
    • (1998) J. Org. Chem. , vol.63 , pp. 5031
    • Xu, Z.1    Lu, X.2
  • 26
    • 0036495319 scopus 로고    scopus 로고
    • For the synthesis of dihydrofurans and dihydropyrroles by RCM, see:
    • For the synthesis of dihydrofurans and dihydropyrroles by RCM, see: Wakamatsu H., Blechert S. Angew. Chem., Int. Ed. 41:2002;794.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 794
    • Wakamatsu, H.1    Blechert, S.2
  • 32
    • 1542364214 scopus 로고    scopus 로고
    • note
    • Synthesis of allyl ether 1a:To a stirred solution of the corresponding Baylis-Hillman acetate (500 mg, 2 mmol) in THF (3 mL) was added DABCO (452 mg, 4 mmol) and stirred for 10 min at rt. To the reaction mixture was added allyl alcohol (1.5 mL) and heated to 50-60°C for 3 days. After usual workup process and column chromatographic purification process (hexane/ether, 30:1) we could obtain the desired compound 1a in 71% isolated yield (350 mg). Other compounds 1b and 1c were synthesized by using the same experimental procedure. The spectroscopic data of prepared compounds are listed below.
  • 33
    • 0036423026 scopus 로고    scopus 로고
    • For the RCM reaction involving the styryl moiety, see:
    • For the RCM reaction involving the styryl moiety, see: Maishal T.K., Sarkar A. Synlett. 2002;1925.
    • (2002) Synlett , pp. 1925
    • Maishal, T.K.1    Sarkar, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.