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Volumn 77, Issue 1, 2009, Pages 201-206

An efficient synthetic method for 3-bromofuran derivatives via stereoselective cyclization of γ, δ-epoxy-(E)-α-bromoacrylates

Author keywords

(E) Bromoacrylate; 3 Bromofuran; 3 Substituted Furan; Cyclization; Furan Synthesis

Indexed keywords


EID: 65549102775     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)25     Document Type: Article
Times cited : (3)

References (26)
  • 1
    • 0001176061 scopus 로고    scopus 로고
    • Katritzky A.R., Ress C.W., and Scriven E.F.V. (Eds), Pergamon, Oxford
    • Keay B.A., and Dibble P.W. In: Katritzky A.R., Ress C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1997), Pergamon, Oxford 395-436
    • (1997) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 395-436
    • Keay, B.A.1    Dibble, P.W.2
  • 2
    • 33845374099 scopus 로고
    • For reviews, see:
    • For reviews, see:. Lipshutz B.H. Chem. Rev. 86 (1986) 795
    • (1986) Chem. Rev. , vol.86 , pp. 795
    • Lipshutz, B.H.1
  • 7
    • 0037059436 scopus 로고    scopus 로고
    • For selected examples of cycloisomerization approaches to furans, see:
    • For selected examples of cycloisomerization approaches to furans, see:. Kel'in A.V., and Gevorgyan V. J. Org. Chem. 67 (2002) 95
    • (2002) J. Org. Chem. , vol.67 , pp. 95
    • Kel'in, A.V.1    Gevorgyan, V.2
  • 10
    • 23044485049 scopus 로고    scopus 로고
    • For recent examples of bromofuran synthesis, see:
    • For recent examples of bromofuran synthesis, see:. Sromek A.W., Rubina M., and Gevorgyan V. J. Am. Chem. Soc 127 (2005) 10500
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 10500
    • Sromek, A.W.1    Rubina, M.2    Gevorgyan, V.3
  • 15
    • 65549134455 scopus 로고    scopus 로고
    • note
    • 2O is not originally assigned 5-hydroxy allenic ester,7 but the furan 4.
  • 17
    • 65549152609 scopus 로고    scopus 로고
    • note
    • The reaction without addition of water resulted in lower yield (<51%).
  • 19
    • 65549139979 scopus 로고    scopus 로고
    • note
    • 2Br in THF
  • 20
    • 4544342275 scopus 로고    scopus 로고
    • Preparation of 11 from 8 by the Olpp and Brückner method with diphenoxybromophosphonoacetate resulted in lower E-selectivity of 11 (E/Z = 77:23)
    • Preparation of 11 from 8 by the Olpp and Brückner method with diphenoxybromophosphonoacetate resulted in lower E-selectivity of 11 (E/Z = 77:23). Olpp T., and Brückner R. Synthesis (2004) 2135
    • (2004) Synthesis , pp. 2135
    • Olpp, T.1    Brückner, R.2
  • 21
    • 65549167590 scopus 로고    scopus 로고
    • note
    • 4 and concentrated. The crude product was purified by flash column chromatography on silica gel (hexane/EtOAc = 85:15) to give 13 (25.0 mg, 75%) as a pale yellow oil.
  • 22
    • 65549122728 scopus 로고    scopus 로고
    • note
    • 2 (dimethyl(1,1,1,3,3,3-hexafluoro-2-propanolato)aluminum.
  • 23
    • 65549170810 scopus 로고    scopus 로고
    • note
    • 2CHOH was changed in 3:1,3:2, 1:1, and 1:2, 14 was obtained in 76%, 92%, 77%, and <20% yield, respectively.
  • 24
    • 65549103125 scopus 로고    scopus 로고
    • note
    • 4 and concentrated. The crude product was purified by flash column chromatography on silica gel (hexane/EtOAc = 8:2) to give 14 (32.7 mg, 92%) as a pale yellow oil.
  • 25
    • 65549113187 scopus 로고    scopus 로고
    • note
    • 2, 0 °C).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.