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Volumn 8, Issue 17, 2006, Pages 3881-3884

Efficient synthesis of 1,3,5-trisubstituted (pyrrol-2-yl)acetic acid esters via dual nucleophilic reactions of sulfonamides or carbamate with 4-trimethyl-siloxy-(5E)-hexen-2-ynoates: Lewis acid catalyzed SN1 and intramolecular Michael addition

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EID: 33748614871     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0616485     Document Type: Article
Times cited : (26)

References (36)
  • 4
    • 0034902213 scopus 로고    scopus 로고
    • For blockbuster drugs of substituted pyrroles, see, e.g.: Thompson, R. B. FASEB J. 2001, 15, 1671-1675.
    • (2001) FASEB J. , vol.15 , pp. 1671-1675
    • Thompson, R.B.1
  • 5
    • 33748603566 scopus 로고    scopus 로고
    • See also refs 14 and 15
    • See also refs 14 and 15.
  • 7
    • 24944474895 scopus 로고    scopus 로고
    • For recent leading references of pyrrole synthesis using alkyne derivatives, see: (a) Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664-5667.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 5664-5667
    • Larionov, O.V.1    De Meijere, A.2
  • 20
    • 33748602216 scopus 로고    scopus 로고
    • note
    • See refs 4d and 4j; ref 4k is also concerned with (pyrrol-2-yl)acetic acids synthesis, which however required several steps.
  • 25
    • 33748584147 scopus 로고    scopus 로고
    • note
    • Ten substrates (1a-j) were prepared as follows: to a solution of ethyl propiolate in THF was added BuLi at -78 °C, and the mixture was stirred at that temperature for 15 min. To this mixture was added enone at -78 °C followed by stirring at -78 - 0 °C for 4.5 h. After the usual workup, the alcohol product was purified by column chromatography and silylated in the usual way (TMS-Cl, imidazole, THF, 0 °C to rt, 0.5 h) to give 1, which was purified by column chromatography prior to use. The % yields of 1 depended on the structure of enones. For the experimental detail and spectroscopic data. see Supporting Information.
  • 26
    • 33748631114 scopus 로고    scopus 로고
    • note
    • These sulfonamides are commercially available.
  • 27
    • 33748624977 scopus 로고    scopus 로고
    • note
    • For discussion about stereocontrol of this kind, see ref 6.
  • 28
    • 2542472142 scopus 로고
    • N2 reactions with amines or Mitsunobu reactions of the alcohols. In addition, the syntheses of the alcohols were specified to individual methods according to both kind and position of desired substituents: Koerner, M.; Rickborn, B. J. Org. Chem. 1989, 54, 9-10.
    • (1989) J. Org. Chem. , vol.54 , pp. 9-10
    • Koerner, M.1    Rickborn, B.2
  • 29
    • 33748617973 scopus 로고    scopus 로고
    • note
    • N1 process must wait for future studies.
  • 31
    • 33748590903 scopus 로고    scopus 로고
    • note
    • For discussion about the lower basicity of disiloxane, see ref 12 and references therein.
  • 35
  • 36
    • 0026418434 scopus 로고
    • Trost, B. M. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.