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Volumn 73, Issue 21, 2008, Pages 8583-8586

Zwitterionic phosphonium sulfonates as easily phase-separable ion-tagged wittig reagents

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ESTERS; HYDROCARBONS; ORGANIC COMPOUNDS;

EID: 55249123580     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801418a     Document Type: Article
Times cited : (23)

References (49)
  • 11
    • 0037835827 scopus 로고    scopus 로고
    • For reviews, see: c
    • For reviews, see: (c) Zhang, W. Tetrahedron 2003, 59, 4475;
    • (2003) Tetrahedron , vol.59 , pp. 4475
    • Zhang, W.1
  • 12
    • 2942545969 scopus 로고    scopus 로고
    • Chem. Rev. 2004, 104, 2531.
    • (2004) Chem. Rev , vol.104 , pp. 2531
  • 22
    • 55249123231 scopus 로고    scopus 로고
    • While NaBr was formed in the formation of 3, its presence appeared to be innocuous as it had no significant influence to the Wittig reaction
    • While NaBr was formed in the formation of 3, its presence appeared to be innocuous as it had no significant influence to the Wittig reaction.
  • 23
    • 0026649673 scopus 로고    scopus 로고
    • Several syntheses of 5j using the classical Wittig reaction of the corresponding triphenylphosphonium salt of 3b have been reported. The reaction required strong base (n-BuLi or t-BuOK) in THF at low temperature and had yields ranging from 60% to 92% with E/Z ratios between 1:1 and 1:2.8. (a) Ali, M. A.; Kondo, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 1130-6.
    • Several syntheses of 5j using the classical Wittig reaction of the corresponding triphenylphosphonium salt of 3b have been reported. The reaction required strong base (n-BuLi or t-BuOK) in THF at low temperature and had yields ranging from 60% to 92% with E/Z ratios between 1:1 and 1:2.8. (a) Ali, M. A.; Kondo, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 1130-6.
  • 27
    • 32344433949 scopus 로고    scopus 로고
    • Kurti, L, Czako, B, Eds, Elsevier Academic Press: Burlington, MA, and references cited therein
    • Kurti, L., Czako, B., Eds. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: Burlington, MA, 2005; pp 212-3, and references cited therein.
    • (2005) Strategic Applications of Named Reactions in Organic Synthesis , pp. 212-213
  • 29
    • 0025601760 scopus 로고    scopus 로고
    • For examples of Z- to E-isomerization, see: (a) Miyata, O, Shinada, T, Ninomiya, I, Naito, T. Synthesis 1990, 1123
    • For examples of Z- to E-isomerization, see: (a) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Synthesis 1990, 1123.
  • 37
    • 0032558647 scopus 로고    scopus 로고
    • The sulfonate group is more robust than, for example, the carboxylic acid group to reduction by alane or silane. See: a
    • The sulfonate group is more robust than, for example, the carboxylic acid group to reduction by alane or silane. See: (a) Russell, M. G.; Warren, S. Tetrahedron Lett. 1998, 39, 7995.
    • (1998) Tetrahedron Lett , vol.39 , pp. 7995
    • Russell, M.G.1    Warren, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.