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Volumn 70, Issue 22, 2005, Pages 9074-9076

A convenient oxazole C-2 protecting group: The synthesis of 4- and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles

Author keywords

[No Author keywords available]

Indexed keywords

METALLIC COMPOUNDS; MOLECULAR STRUCTURE; REMOVAL; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 27444445014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051490m     Document Type: Article
Times cited : (24)

References (18)
  • 1
    • 27444436261 scopus 로고    scopus 로고
    • Merck Research Laboratories 2003 UNCF Summer Intern
    • Merck Research Laboratories 2003 UNCF Summer Intern.
  • 2
    • 12344258124 scopus 로고    scopus 로고
    • and references therein
    • For a recent reviews see: Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376 and references therein.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 376
    • Schlosser, M.1
  • 4
    • 84970612132 scopus 로고
    • J. Wiley and Sons: New York
    • a of the C-2 H has been estimated to be ∼20. For a general review of oxazoles see: (a) Turchi, I. J., Ed. Heterocyclic Compounds; J. Wiley and Sons: New York, 1986.
    • (1986) Heterocyclic Compounds
    • Turchi, I.J.1
  • 5
    • 0004246795 scopus 로고    scopus 로고
    • J. Wiley and Sons: New York, Parts A and B
    • (b) Palmer, D., Ed. Heterocyclic Compounds; J. Wiley and Sons: New York, 2003, 2004; Vol. 60, Parts A and B.
    • (2003) Heterocyclic Compounds , vol.60
    • Palmer, D.1
  • 8
    • 27444444313 scopus 로고    scopus 로고
    • Reference 5
    • (b) Reference 5.
  • 14
    • 0025898470 scopus 로고
    • Whitney, S. E.; Rickborn, B. J. Org. Chem. 1991, 56, 3058. This paper reports they were unable to prepare 2-(trimethylsilyl)-4-phenyloxazole via the reported literature methodology of O-Si to C-Si isomerization. See refs 4a and 4b in that paper.
    • (1991) J. Org. Chem. , vol.56 , pp. 3058
    • Whitney, S.E.1    Rickborn, B.2
  • 17
    • 0035929944 scopus 로고    scopus 로고
    • TIPSOTf contained 5-10% of n-propyldiisopropylsilyl triflate, which complicated the NMR spectrum but not the subsequent chemistry. A similar observation about the purity of TIPSOTF was previously made: Barden, D. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 2001, 2366.
    • (2001) J. Chem. Soc., Chem. Commun. , pp. 2366
    • Barden, D.J.1    Fleming, I.2
  • 18
    • 0042869554 scopus 로고    scopus 로고
    • For a thorough review of the triisopropylsilyl group, see: Rucker, C. Chem. Rev. 2005, 95, 1009.
    • (2005) Chem. Rev. , vol.95 , pp. 1009
    • Rucker, C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.